Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions

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2. Li-Juan Yu, Michelle L. Coote. Electrostatic Switching of Stereoselectivity in Aldol Reactions. The Journal of Organic Chemistry 2021, 86 (13) , 9076-9083. https://doi.org/10.1021/acs.joc.1c01032
3. Mao Cai, Kaini Xu, Yuze Li, Zongxiu Nie, Long Zhang, Sanzhong Luo. Chiral Primary Amine/Ketone Cooperative Catalysis for Asymmetric α-Hydroxylation with Hydrogen Peroxide. Journal of the American Chemical Society 2021, 143 (2) , 1078-1087. https://doi.org/10.1021/jacs.0c11787
4. Victor Wambua, Jennifer S. Hirschi, Mathew J. Vetticatt. Rapid Evaluation of the Mechanism of Buchwald–Hartwig Amination and Aldol Reactions Using Intramolecular 13C Kinetic Isotope Effects. ACS Catalysis 2021, 11 (1) , 60-67. https://doi.org/10.1021/acscatal.0c04752
5. Kenta Stier, Marek P. Checinski, Swjatoslaw N. R. Witte, Rainer Mahrwald. Matched/Mismatched Cases in Proline-Catalyzed Cascade Reactions with Carbohydrates: A Computational Insight into the Role of d- and l-Proline. The Journal of Organic Chemistry 2019, 84 (3) , 1201-1217. https://doi.org/10.1021/acs.joc.8b02530
6. Jing Wang, Zhi-Xiong Deng, Chao-Ming Wang, Peng-Ju Xia, Jun-An Xiao, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang. Unraveling and Manipulating the Stereospecific Retro-Aldol Reaction in the Organocatalytic Asymmetric Aldol Reaction of Isatin and Cyclohexanone. Organic Letters 2018, 20 (23) , 7535-7538. https://doi.org/10.1021/acs.orglett.8b03292
7. Keitou Shu, Thomas Kodadek. Solid-Phase Synthesis of β-Hydroxy Ketones Via DNA-Compatible Organocatalytic Aldol Reactions. ACS Combinatorial Science 2018, 20 (5) , 277-281. https://doi.org/10.1021/acscombsci.8b00001
8. Yujiro Hayashi, Tatsuya Yamazaki, Genki Kawauchi, Itaru Sato. Prolinate Salt as a Catalyst in the syn-Selective, Asymmetric Mannich Reaction of Alkynyl Imine. Organic Letters 2018, 20 (8) , 2391-2394. https://doi.org/10.1021/acs.orglett.8b00728
9. Yifei Li, Kelvin E. Jackson, Andrew Charlton, Ben Le Neve-Foster, Asma Khurshid, Heinrich-K. A. Rudy, Amber L. Thompson, Robert S. Paton, and David. M. Hodgson . Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment. The Journal of Organic Chemistry 2017, 82 (19) , 10479-10488. https://doi.org/10.1021/acs.joc.7b01954
10. Yujiro Hayashi, Nariyoshi Umekubo, and Taku Hirama . Prolinate Salts as Catalysts for α-Aminoxylation of Aldehyde and Associated Mechanistic Insights. Organic Letters 2017, 19 (16) , 4155-4158. https://doi.org/10.1021/acs.orglett.7b01433
11. Sheng Zhang, Lide Cha, Lijun Li, Yanbin Hu, Yanan Li, Zhenggen Zha, and Zhiyong Wang . Asymmetric Formal Aza-Diels–Alder Reaction of Trifluoromethyl Hemiaminals with Enones Catalyzed by Primary Amines. The Journal of Organic Chemistry 2016, 81 (8) , 3177-3187. https://doi.org/10.1021/acs.joc.6b00087
12. Zhen Li, Xin Li, Xiang Ni, and Jin-Pei Cheng . Equilibrium Acidities of Proline Derived Organocatalysts in DMSO. Organic Letters 2015, 17 (5) , 1196-1199. https://doi.org/10.1021/acs.orglett.5b00143
13. Yu-hong Lam and K. N. Houk . Origins of Stereoselectivity in Intramolecular Aldol Reactions Catalyzed by Cinchona Amines. Journal of the American Chemical Society 2015, 137 (5) , 2116-2127. https://doi.org/10.1021/ja513096x
14. Hannes Erdmann, Feng An, Peter Mayer, Armin R. Ofial, Sami Lakhdar, and Herbert Mayr . Structures and Reactivities of 2-Trityl- and 2-(Triphenylsilyl)pyrrolidine-Derived Enamines: Evidence for Negative Hyperconjugation with the Trityl Group. Journal of the American Chemical Society 2014, 136 (40) , 14263-14269. https://doi.org/10.1021/ja508065e
15. Zhe An, Ying Guo, Liwei Zhao, Zhi Li, and Jing He . l-Proline-Grafted Mesoporous Silica with Alternating Hydrophobic and Hydrophilic Blocks to Promote Direct Asymmetric Aldol and Knoevenagel–Michael Cascade Reactions. ACS Catalysis 2014, 4 (8) , 2566-2576. https://doi.org/10.1021/cs500385s
16. Jingqi Guan, Bo Liu, Xiaoyuan Yang, Jing Hu, Chunhua Wang, and Qiubin Kan . Immobilization of Proline onto Al-SBA-15 for C–C Bond-Forming Reactions. ACS Sustainable Chemistry & Engineering 2014, 2 (4) , 925-933. https://doi.org/10.1021/sc4005247
17. Xiao-Song Xue, Chen Yang, Xin Li, and Jin-Pei Cheng . Computational Study on the pKa Shifts in Proline Induced by Hydrogen-Bond-Donating Cocatalysts. The Journal of Organic Chemistry 2014, 79 (3) , 1166-1173. https://doi.org/10.1021/jo402605n
18. Milan Bergeron-Brlek, Timothy Teoh, and Robert Britton . A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis. Organic Letters 2013, 15 (14) , 3554-3557. https://doi.org/10.1021/ol401370b
19. Sameer Hussain, Siddhartha De, and Parameswar Krishnan Iyer . Thiazole-Containing Conjugated Polymer as a Visual and Fluorometric Sensor for Iodide and Mercury. ACS Applied Materials & Interfaces 2013, 5 (6) , 2234-2240. https://doi.org/10.1021/am400123j
20. Akhilesh K. Sharma and Raghavan B. Sunoj . Refined Transition-State Models for Proline-Catalyzed Asymmetric Michael Reactions under Basic and Base-Free Conditions. The Journal of Organic Chemistry 2012, 77 (23) , 10516-10524. https://doi.org/10.1021/jo3023654
21. Taewoo Min, James C. Fettinger, and Annaliese K. Franz . Enantiocontrol with a Hydrogen-bond Directing Pyrrolidinylsilanol Catalyst. ACS Catalysis 2012, 2 (8) , 1661-1666. https://doi.org/10.1021/cs300290j
22. Miglena K. Georgieva, Filipe J. S. Duarte, Margarida V. B. Queirós, and A. Gil Santos . Catalytic Asymmetric 5-enolexo Aldolizations. A Computational Study. The Journal of Organic Chemistry 2012, 77 (13) , 5569-5576. https://doi.org/10.1021/jo300633y
23. Xiangting Sun, Rongxiu Zhu, Jun Gao, Dongju Zhang, and Dacheng Feng . Theoretical Elucidation on the Regio-, Diastereo-, and Enantio-Selectivities of Chiral Primary–Tertiary Diamine Catalyst for Asymmetric Direct Aldol Reactions of Aliphatic Ketones. The Journal of Physical Chemistry A 2012, 116 (26) , 7082-7088. https://doi.org/10.1021/jp2124873
24. Jordi Burés, Alan Armstrong, and Donna G. Blackmond . Curtin–Hammett Paradigm for Stereocontrol in Organocatalysis by Diarylprolinol Ether Catalysts. Journal of the American Chemical Society 2012, 134 (15) , 6741-6750. https://doi.org/10.1021/ja300415t
25. Jason E. Hein, Jordi Burés, Yu-hong Lam, Matthew Hughes, K. N. Houk, Alan Armstrong, and Donna G. Blackmond . Enamine Carboxylates as Stereodetermining Intermediates in Prolinate Catalysis. Organic Letters 2011, 13 (20) , 5644-5647. https://doi.org/10.1021/ol2023533
26. Annhelen Lu, Thomas P. Smart, Thomas H. Epps, III, Deborah A. Longbottom, and Rachel K. O’Reilly . l-Proline Functionalized Polymers Prepared by RAFT Polymerization and Their Assemblies as Supported Organocatalysts. Macromolecules 2011, 44 (18) , 7233-7241. https://doi.org/10.1021/ma201256m
27. Hui Yang and Ming Wah Wong . β-Amino Acid Catalyzed Asymmetric Michael Additions: Design of Organocatalysts with Catalytic Acid/Base Dyad Inspired by Serine Proteases. The Journal of Organic Chemistry 2011, 76 (18) , 7399-7405. https://doi.org/10.1021/jo2011413
28. Louis Marchetti and Mindy Levine . Biomimetic Catalysis. ACS Catalysis 2011, 1 (9) , 1090-1118. https://doi.org/10.1021/cs200171u
29. Suzanne M. Opalka, Jeremy L. Steinbacher, Brandon A. Lambiris, and D. Tyler McQuade . Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View. The Journal of Organic Chemistry 2011, 76 (16) , 6503-6517. https://doi.org/10.1021/jo200838v
30. Paul Ha-Yeon Cheong, Claude Y. Legault, Joann M. Um, Nihan Çelebi-Ölçüm, and K. N. Houk . Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities. Chemical Reviews 2011, 111 (8) , 5042-5137. https://doi.org/10.1021/cr100212h
31. Esther N. Pesciotta, Darryl J. Bornhop, and Robert A. Flowers, II . Backscattering Interferometry: An Alternative Approach for the Study of Hydrogen Bonding Interactions in Organic Solvents. Organic Letters 2011, 13 (10) , 2654-2657. https://doi.org/10.1021/ol200757a
32. Markus B. Schmid, Kirsten Zeitler, and Ruth M. Gschwind . NMR Investigations on the Proline-Catalyzed Aldehyde Self-Condensation: Mannich Mechanism, Dienamine Detection, and Erosion of the Aldol Addition Selectivity. The Journal of Organic Chemistry 2011, 76 (9) , 3005-3015. https://doi.org/10.1021/jo200431v
33. Pablo Domínguez de María, Paula Bracco, Luiz Fernando Castelhano, and Gerrald Bargeman . Influence of the Organocatalyst in the Aldol/Mannich-Type Product Selectivities in C−C Bond Forming Reactions. ACS Catalysis 2011, 1 (2) , 70-75. https://doi.org/10.1021/cs100088m
34. Hua Yang and Rich G. Carter. Synthesis of All-Carbon, Quaternary Center-Containing Cyclohexenones through an Organocatalyzed, Multicomponent Coupling. Organic Letters 2010, 12 (13) , 3108-3111. https://doi.org/10.1021/ol1011955
35. Donna G. Blackmond, Antonio Moran, Matthew Hughes and Alan Armstrong . Unusual Reversal of Enantioselectivity in the Proline-Mediated α-Amination of Aldehydes Induced by Tertiary Amine Additives. Journal of the American Chemical Society 2010, 132 (22) , 7598-7599. https://doi.org/10.1021/ja102718x
36. Dhevalapally B. Ramachary and Y. Vijayendar Reddy. A General Approach to Chiral Building Blocks via Direct Amino Acid-Catalyzed Cascade Three-Component Reductive Alkylations: Formal Total Synthesis of HIV-1 Protease Inhibitors, Antibiotic Agglomerins, Brefeldin A, and (R)-γ-Hexanolide. The Journal of Organic Chemistry 2010, 75 (1) , 74-85. https://doi.org/10.1021/jo901799n
37. Mauro De Nisco, Silvana Pedatella, Hidayat Ullah, Javid H. Zaidi, Daniele Naviglio, Özgür Özdamar and Romualdo Caputo . Proline−β3-Amino-Ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium. The Journal of Organic Chemistry 2009, 74 (24) , 9562-9565. https://doi.org/10.1021/jo902106r
38. María-Cruz Bonache, Alessandra Cordeiro, Paula Carrero, Ernesto Quesada, María-José Camarasa, María-Luisa Jimeno and Ana San-Félix . One-Pot Synthesis of Polycyclic Nucleosides with Unusual Molecular Skeletons. The Journal of Organic Chemistry 2009, 74 (23) , 9071-9081. https://doi.org/10.1021/jo9019144
39. Alan Armstrong, Yunas Bhonoah and Andrew J. P. White. Constrained β-Proline Analogues in Organocatalytic Aldol Reactions: The Influence of Acid Geometry. The Journal of Organic Chemistry 2009, 74 (14) , 5041-5048. https://doi.org/10.1021/jo900840v
40. Hui Zhu, Fernando R. Clemente, K. N. Houk and Matthew P. Meyer . Rate Limiting Step Precedes C−C Bond Formation in the Archetypical Proline-Catalyzed Intramolecular Aldol Reaction. Journal of the American Chemical Society 2009, 131 (5) , 1632-1633. https://doi.org/10.1021/ja806672y
41. Gabriela Guillena, Maria del Carmen Hita, Carmen Nájera and Santiago F. Viózquez. A Highly Efficient Solvent-Free Asymmetric Direct Aldol Reaction Organocatalyzed by Recoverable (S)-Binam-l-Prolinamides. ESI-MS Evidence of the Enamine−Iminium Formation. The Journal of Organic Chemistry 2008, 73 (15) , 5933-5943. https://doi.org/10.1021/jo800773q
42. Jia-Rong Chen, Xiao-Lei An, Xiao-Yu Zhu, Xu-Fan Wang and Wen-Jing Xiao. Rational Combination of Two Privileged Chiral Backbones: Highly Efficient Organocatalysts for Asymmetric Direct Aldol Reactions between Aromatic Aldehydes and Acylic Ketones. The Journal of Organic Chemistry 2008, 73 (15) , 6006-6009. https://doi.org/10.1021/jo800910s
43. Aiping Fu, Hongliang Li, Shuping Yuan, Hongzong Si and Yunbo Duan. Origins of Opposite Syn−Anti Diastereoselectivities in Primary and Secondary Amino Acid-Catalyzed Intermolecular Aldol Reactions Involving Unmodified α-Hydroxyketones. The Journal of Organic Chemistry 2008, 73 (14) , 5264-5271. https://doi.org/10.1021/jo800089q
44. Saumen Hajra and Aswini Kumar Giri. Organocatalytic and Enantioselective Synthesis of β-(Hydroxyalkyl)-γ-Butyrolactones. The Journal of Organic Chemistry 2008, 73 (10) , 3935-3937. https://doi.org/10.1021/jo8005733
45. Valerio D'Elia,, Hans Zwicknagl, and, Oliver Reiser. Short α/β-Peptides as Catalysts for Intra- and Intermolecular Aldol Reactions. The Journal of Organic Chemistry 2008, 73 (8) , 3262-3265. https://doi.org/10.1021/jo800168h
46. Barbara Nozière and, Armando Córdova. A Kinetic and Mechanistic Study of the Amino Acid Catalyzed Aldol Condensation of Acetaldehyde in Aqueous and Salt Solutions. The Journal of Physical Chemistry A 2008, 112 (13) , 2827-2837. https://doi.org/10.1021/jp7096845
47. Abigail G. Doyle and, Eric N. Jacobsen. Small-Molecule H-Bond Donors in Asymmetric Catalysis. Chemical Reviews 2007, 107 (12) , 5713-5743. https://doi.org/10.1021/cr068373r
48. Santanu Mukherjee,, Jung Woon Yang,, Sebastian Hoffmann, and, Benjamin List. Asymmetric Enamine Catalysis. Chemical Reviews 2007, 107 (12) , 5471-5569. https://doi.org/10.1021/cr0684016
49. Natalia Zotova,, Axel Franzke,, Alan Armstrong, and, Donna G. Blackmond. Clarification of the Role of Water in Proline-Mediated Aldol Reactions. Journal of the American Chemical Society 2007, 129 (49) , 15100-15101. https://doi.org/10.1021/ja0738881
50. Dhevalapally B. Ramachary and, Mamillapalli Kishor. Organocatalytic Sequential One-Pot Double Cascade Asymmetric Synthesis of Wieland−Miescher Ketone Analogues from a Knoevenagel/Hydrogenation/Robinson Annulation Sequence:  Scope and Applications of Organocatalytic Biomimetic Reductions. The Journal of Organic Chemistry 2007, 72 (14) , 5056-5068. https://doi.org/10.1021/jo070277i
51. Dorota Gryko,, Magdalena Zimnicka, and, Radosław Lipiński. Brønsted Acids as Additives for the Direct Asymmetric Aldol Reaction Catalyzed by l-Prolinethioamides. Direct Evidence for Enamine−Iminium Catalysis. The Journal of Organic Chemistry 2007, 72 (3) , 964-970. https://doi.org/10.1021/jo062149k
52. Yongjun Liu,, Roberto Melgar-Fernández, and, Eusebio Juaristi. Enantioselective Amination of α-Phenyl-α-cyanoacetate Catalyzed by Chiral Amines Incorporating the α-Phenylethyl Auxiliary. The Journal of Organic Chemistry 2007, 72 (4) , 1522-1525. https://doi.org/10.1021/jo0622633
53. Takashi Nagamine,, Kohei Inomata,, Yasuyuki Endo, and, Leo A. Paquette. Amino Acid Mediated Intramolecular Asymmetric Aldol Reaction to Construct a New Chiral Bicyclic Enedione Containing a Seven-Membered Ring:  Remarkable Inversion of Enantioselectivity Compared to the Six-Membered Ring Example. The Journal of Organic Chemistry 2007, 72 (1) , 123-131. https://doi.org/10.1021/jo061824n
54. Yan Zhou and, Zixing Shan. Chiral Diols:  A New Class of Additives for Direct Aldol Reaction Catalyzed by l-Proline. The Journal of Organic Chemistry 2006, 71 (25) , 9510-9512. https://doi.org/10.1021/jo060802y
55. Jia-Rong Chen,, Xin-Yong Li,, Xiao-Ning Xing, and, Wen-Jing Xiao. Sterically and Electronically Tunable and Bifunctional Organocatalysts:  Design and Application in Asymmetric Aldol Reaction of Cyclic Ketones with Aldehydes. The Journal of Organic Chemistry 2006, 71 (21) , 8198-8202. https://doi.org/10.1021/jo0615089
56. Narayan S. Karanjule,, Shankar D. Markad,, Vaishali S. Shinde, and, Dilip D. Dhavale. Intramolecular 5-endo-Trig Aminomercuration of β-Hydroxy-γ-alkenylamines:  Efficient Route to a Pyrrolidine Ring and Its Application for the Synthesis of (+)-Castanospermine and Analogues. The Journal of Organic Chemistry 2006, 71 (12) , 4667-4670. https://doi.org/10.1021/jo0601617
57. Mathieu Lemay and, William W. Ogilvie. Mechanistic Studies of Hydrazide-Catalyzed Enantioselective Diels−Alder Reactions. The Journal of Organic Chemistry 2006, 71 (12) , 4663-4666. https://doi.org/10.1021/jo060339p
58. Benito Alcaide,, Pedro Almendros,, Amparo Luna, and, M. Rosario Torres. Proline-Catalyzed Diastereoselective Direct Aldol Reaction between 4-Oxoazetidine-2-carbaldehydes and Ketones. The Journal of Organic Chemistry 2006, 71 (13) , 4818-4822. https://doi.org/10.1021/jo0604235
59. Ruth Gordillo and, K. N. Houk. Origins of Stereoselectivity in Diels−Alder Cycloadditions Catalyzed by Chiral Imidazolidinones. Journal of the American Chemical Society 2006, 128 (11) , 3543-3553. https://doi.org/10.1021/ja0525859
60. Jean-Luc Vasse,, Antoine Joosten,, Clément Denhez, and, Jan Szymoniak. Stereoselective Synthesis of Pyrrolidines from N-Allyl Oxazolidines via Hydrozirconation−Cyclization. Organic Letters 2005, 7 (22) , 4887-4889. https://doi.org/10.1021/ol0517776
61. Noriaki Itagaki,, Mari Kimura,, Tsutomu Sugahara, and, Yoshiharu Iwabuchi. Organocatalytic Entry to Chiral Bicyclo[3.n.1]alkanones via Direct Asymmetric Intramolecular Aldolization. Organic Letters 2005, 7 (19) , 4185-4188. https://doi.org/10.1021/ol051569d
62. Jia-Rong Chen,, Hai-Hua Lu,, Xin-Yong Li,, Lin Cheng,, Jian Wan, and, Wen-Jing Xiao. Readily Tunable and Bifunctional l-Prolinamide Derivatives:  Design and Application in the Direct Enantioselective Aldol Reactions. Organic Letters 2005, 7 (20) , 4543-4545. https://doi.org/10.1021/ol0520323
63. Fernando R. Clemente and, K. N. Houk. Theoretical Studies of Stereoselectivities of Intramolecular Aldol Cyclizations Catalyzed by Amino Acids. Journal of the American Chemical Society 2005, 127 (32) , 11294-11302. https://doi.org/10.1021/ja0507620
64. Aleksey I. Gerasyuto,, Richard P. Hsung,, Nadiya Sydorenko, and, Brian Slafer. A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts. The Journal of Organic Chemistry 2005, 70 (11) , 4248-4256. https://doi.org/10.1021/jo050171s
65. Kohei Inomata,, Matthieu Barragué, and, Leo A. Paquette. Diastereoselectivities Realized in the Amino Acid Catalyzed Aldol Cyclizations of Triketo Acetonides of Differing Ring Size. The Journal of Organic Chemistry 2005, 70 (2) , 533-539. https://doi.org/10.1021/jo0486084
66. Yujiro Hayashi,, Junichiro Yamaguchi,, Tatsunobu Sumiya,, Kazuhiro Hibino, and, Mitsuru Shoji. Direct Proline-Catalyzed Asymmetric α-Aminoxylation of Aldehydes and Ketones. The Journal of Organic Chemistry 2004, 69 (18) , 5966-5973. https://doi.org/10.1021/jo049338s
67. Christophe Allemann,, Ruth Gordillo,, Fernando R. Clemente,, Paul Ha-Yeon Cheong, and, K. N. Houk. Theory of Asymmetric Organocatalysis of Aldol and Related Reactions:  Rationalizations and Predictions. Accounts of Chemical Research 2004, 37 (8) , 558-569. https://doi.org/10.1021/ar0300524
68. Benjamin List. Enamine Catalysis Is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents. Accounts of Chemical Research 2004, 37 (8) , 548-557. https://doi.org/10.1021/ar0300571
69. Susumu Saito and, Hisashi Yamamoto. Design of Acid−Base Catalysis for the Asymmetric Direct Aldol Reaction. Accounts of Chemical Research 2004, 37 (8) , 570-579. https://doi.org/10.1021/ar030064p
70. Atwood K. Cheung,, Ryan Murelli, and, Marc L. Snapper. Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A2 Inhibition. The Journal of Organic Chemistry 2004, 69 (17) , 5712-5719. https://doi.org/10.1021/jo049285e
71. Nicola Vignola and, Benjamin List. Catalytic Asymmetric Intramolecular α-Alkylation of Aldehydes. Journal of the American Chemical Society 2004, 126 (2) , 450-451. https://doi.org/10.1021/ja0392566
72. Jason E. Imbriglio,, Melissa M. Vasbinder, and, Scott J. Miller. Dual Catalyst Control in the Amino Acid-Peptide-Catalyzed Enantioselective Baylis−Hillman Reaction. Organic Letters 2003, 5 (20) , 3741-3743. https://doi.org/10.1021/ol035466b
73. Koichi Mikami and, Masahiro Yamanaka. Symmetry Breaking in Asymmetric Catalysis:  Racemic Catalysis to Autocatalysis. Chemical Reviews 2003, 103 (8) , 3369-3400. https://doi.org/10.1021/cr000260z
74. Zhuo Tang,, Fan Jiang,, Luo-Ting Yu,, Xin Cui,, Liu-Zhu Gong,, Ai-Qiao Mi,, Yao-Zhong Jiang, and, Yun-Dong Wu. Novel Small Organic Molecules for a Highly Enantioselective Direct Aldol Reaction. Journal of the American Chemical Society 2003, 125 (18) , 5262-5263. https://doi.org/10.1021/ja034528q
75. Gustavo Senra G. de Carvalho, Douglas C. Alcântara Pinto, Robson Corrêa da Silva, Fernando de Carvalho da Silva. Heterogeneous organocatalysis: the proline case. RSC Advances 2025, 15 (28) , 22469-22504. https://doi.org/10.1039/D5RA02331A
76. Jaibir Singh, Pallavi Garg, Ramasamy Vijaya Anand, Jino George. Cavity Catalysis of an Enantioselective Reaction under Vibrational Strong Coupling. Chemistry – A European Journal 2024, 30 (26) https://doi.org/10.1002/chem.202400607
77. Bert Biesemans, Jeriffa De Clercq, Christian V. Stevens, Joris W. Thybaut, Jeroen Lauwaert. Recent advances in amine catalyzed aldol condensations. Catalysis Reviews 2024, 66 (2) , 401-483. https://doi.org/10.1080/01614940.2022.2048570
78. Tolga A. Yeşil, Taner Atalar, Mustafa Yavuz, Erkan Ertürk. Prolinamides derived from 2-aminocyclohexanols as organocatalysts for asymmetric List-Lerner-Barbas aldol reactions. Tetrahedron Letters 2024, 140 , 155042. https://doi.org/10.1016/j.tetlet.2024.155042
79. Anugam V. Krishna, Shyam D. Sanwal, Sibani Rath, P. R. Lakshmi, Dhevalapally B. Ramachary. Conformation-controlled catalytic asymmetric synthesis of Swaminathan ketones. Green Chemistry 2024, 26 (2) , 771-784. https://doi.org/10.1039/D3GC02975A
80. . Enzymatic C─C Bond Formation by Aldol Reactions. 2024, 1-14. https://doi.org/10.1002/9783527678334.ch1
81. Jie Jack Li. Hajos–Wiechert Reaktion. 2024, 252-254. https://doi.org/10.1007/978-3-031-52850-7_62
82. Chun-Yi Huang, Hsiao-Wei Liao, Teh-Min Hu. Chemical reactivity of the tryptophan/acetone/DMSO triad system and its potential applications in nanomaterial synthesis. RSC Advances 2023, 13 (43) , 29802-29808. https://doi.org/10.1039/D3RA06596K
83. Tolga A. Yeşil, Taner Atalar, Mustafa Yavuz, Erkan Ertürk. Prolinamides containing 2-(2-aminocyclohexyl)phenols as highly enantioselective organocatalysts for aldol reactions. Organic & Biomolecular Chemistry 2023, 21 (28) , 5809-5826. https://doi.org/10.1039/D3OB00723E
84. Efraím Reyes, Liher Prieto, Uxue Uria, Luisa Carrillo, Jose L. Vicario. Asymmetric Dual Enamine Catalysis/Hydrogen Bonding Activation. Catalysts 2023, 13 (7) , 1091. https://doi.org/10.3390/catal13071091
85. Lo’ay Ahmed Al-Momani, Heinrich Lang, Steffen Lüdeke. A Pathway for Aldol Additions Catalyzed by l-Hydroxyproline-Peptides via a β-Hydroxyketone Hemiaminal Intermediate. Chemistry 2023, 5 (2) , 1203-1219. https://doi.org/10.3390/chemistry5020081
86. Bapu R. Thorat, Suraj N. Mali, Swati S. Wavhal, Devidas S. Bhagat, Ravikumar M. Borade, A. Chapolikar, Ajaykumar Gandhi, Pawan Shinde. L-Proline: A Versatile Organo-Catalyst in Organic Chemistry. Combinatorial Chemistry & High Throughput Screening 2023, 26 (6) , 1108-1140. https://doi.org/10.2174/1386207325666220720105845
87. Marco Reinmold, Amin Fahim, Arnim Lühken. Expedition Nobel prize chemistry 2021 – experimental insights into the topic of asymmetric organocatalysis. CHEMKON 2023, 30 (3) , 125-129. https://doi.org/10.1002/ckon.202200028
88. Ángel Martín Pendás, Julia Contreras-García. Molecules. 2023, 221-251. https://doi.org/10.1007/978-3-031-13666-5_6
89. Álvaro F. Magalhães, Matthew W. Powner. Prebiotic triose glycolysis promoted by co-catalytic proline and phosphate in neutral water. Chemical Communications 2022, 58 (97) , 13519-13522. https://doi.org/10.1039/D2CC05466C
90. A. Uyanik, O. Sahin, E. Akceylan, S. Eymur, I. Uyanik, M. Yilmaz. Effect of Calix[4]arene as a Hydrophobic Substituent on Proline Catalysis of Direct Asymmetric Aldol Reactions in the Presence of Water. Russian Journal of General Chemistry 2022, 92 (11) , 2390-2399. https://doi.org/10.1134/S107036322211024X
91. Jee-Yee Chen, Hannah Pineault, Nicholas A. Brunelli. Quantifying the fraction and activity of catalytic sites at different surface densities of aminosilanes in SBA-15 for the aldol reaction and condensation. Journal of Catalysis 2022, 413 , 1048-1055. https://doi.org/10.1016/j.jcat.2022.08.015
92. Lin Cheng, Rui-Jiao Wu, Yi-Ming Li, Hao Ren, Chun-Yan Ji, Wen-Jing Li. Single-chain polymer nanoparticles-encapsulated chiral bifunctional metal-organic frameworks for asymmetric sequential reactions. Inorganic Chemistry Communications 2022, 141 , 109577. https://doi.org/10.1016/j.inoche.2022.109577
93. Nagaraju Kerru, Suresh Maddila, Sreekantha B. Jonnalagadda. Organo-catalysis as emerging tools in organic synthesis: aldol and Michael reactions. Physical Sciences Reviews 2022, 7 (4-5) , 345-371. https://doi.org/10.1515/psr-2021-0023
94. Kantharaju Kamanna. Organocatalysts based on natural and modified amino acids for asymmetric reactions. Physical Sciences Reviews 2022, 7 (4-5) , 429-467. https://doi.org/10.1515/psr-2021-0026
95. Giacomo Botti, Chiara Aieta, Riccardo Conte. The complex vibrational spectrum of proline explained through the adiabatically switched semiclassical initial value representation. The Journal of Chemical Physics 2022, 156 (16) https://doi.org/10.1063/5.0089720
96. Bo Ding, Qilin Xue, Shihu Jia, Hong-Gang Cheng, Qianghui Zhou. Recent Advances in Catalytic Nonenzymatic Kinetic Resolution of Tertiary Alcohols. Synthesis 2022, 54 (07) , 1721-1732. https://doi.org/10.1055/a-1712-0912
97. Efraim Reyes, Qui‐Nhi Duong, Liher Prieto, Olga García Mancheño, José L. Vicario. Assisted and Dual Anion Binding in Amino and Nucleophilic Catalysis. 2022, 271-306. https://doi.org/10.1002/9783527830664.ch9
98. Li-Juan Yu, Mitchell T. Blyth, Michelle L. Coote. Re-Examination of Proline-Catalyzed Intermolecular Aldol Reactions: An Ab Initio Kinetic Modelling Study. Topics in Catalysis 2022, 65 (1-4) , 354-365. https://doi.org/10.1007/s11244-021-01501-5
99. Fabrizio Vetica, Fabiana Pandolfi, Luca Pettazzoni, Francesca Leonelli, Martina Bortolami. Organocatalyst Design for the Stereoselective Annulation towards Bicyclic Diketones and Analogues. Symmetry 2022, 14 (2) , 355. https://doi.org/10.3390/sym14020355
100. Vinod K. Tiwari, Abhijeet Kumar, Sanchayita Rajkhowa, Garima Tripathi, Anil Kumar Singh. Organocatalysis: A Versatile Tool for Asymmetric Green Organic Syntheses. 2022, 261-315. https://doi.org/10.1007/978-981-19-2734-8_7