Direct and Enantioselective Organocatalytic α-Chlorination of AldehydesClick to copy article linkArticle link copied!
Abstract

The first direct enantioselective catalytic α-chlorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective chlorination of aldehydes to generate α-chloro aldehydes, an important chiral synthon for chemical and medicinal agent synthesis. The use of imidazolidinone 3 as the asymmetric catalyst has been found to mediate the halogenation of a large variety of aldehyde substrates with the perchlorinated quinone 1 serving as the electrophilic chlorinating reagent. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. The capacity of catalyst 3 to override the inherent bias of resident stereogenicity in the chlorination of enantiopure β-chiral aldehydes is also described. Catalyst quantities of 5 mol % were generally employed in this study.
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(10)
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- Yi Liu, Sophie G. Bender, Damien Sorigue, Daniel J. Diaz, Andrew D. Ellington, Greg Mann, Simon Allmendinger, Todd K. Hyster. Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins. Journal of the American Chemical Society 2024, 146
(11)
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, 1851-1856. https://doi.org/10.1021/acs.orglett.4c00059
- Zhiyang Li, Baocheng Wang, Chaoshen Zhang, Wai Yam Lo, Liangliang Yang, Jianwei Sun. Catalytic Enantioselective Nucleophilic α-Chlorination of Ketones with NaCl. Journal of the American Chemical Society 2024, 146
(4)
, 2779-2788. https://doi.org/10.1021/jacs.3c12826
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(7)
, 4359-4371. https://doi.org/10.1021/acs.joc.2c02967
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(4)
, 289-305. https://doi.org/10.1021/acsorginorgau.2c00009
- George Hutchinson, Carla Alamillo-Ferrer, Martín Fernández-Pascual, Jordi Burés. Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide. The Journal of Organic Chemistry 2022, 87
(12)
, 7968-7974. https://doi.org/10.1021/acs.joc.2c00600
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(2)
, 1012-1017. https://doi.org/10.1021/acscatal.1c05500
- Yvonne Grell, Xiulan Xie, Sergei I. Ivlev, Eric Meggers. Enantioselective α-Fluorination and α-Chlorination of N-Acyl Pyrazoles Catalyzed by a Non-C2-Symmetric Chiral-at-Rhodium Catalyst. ACS Catalysis 2021, 11
(18)
, 11396-11406. https://doi.org/10.1021/acscatal.1c02901
- George Hutchinson, Carla Alamillo-Ferrer, Jordi Burés. Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes. Journal of the American Chemical Society 2021, 143
(18)
, 6805-6809. https://doi.org/10.1021/jacs.1c02997
- Aika Takeshima, Mio Shimogaki, Taichi Kano, Keiji Maruoka. Development of Ketone-Based Brominating Agents (KBA) for the Practical Asymmetric α-Bromination of Aldehydes Catalyzed by Tritylpyrrolidine. ACS Catalysis 2020, 10
(11)
, 5959-5963. https://doi.org/10.1021/acscatal.0c01596
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(8)
, 3010-3013. https://doi.org/10.1021/acs.orglett.0c00772
- Manjula D. Rathnayake, Jimmie D. Weaver, III. Alkyl Halides via Visible Light Mediated Dehalogenation. Organic Letters 2019, 21
(23)
, 9681-9687. https://doi.org/10.1021/acs.orglett.9b03848
- Tobias Sandmeier, F. Wieland Goetzke, Simon Krautwald, Erick M. Carreira. Iridium-Catalyzed Enantioselective Allylic Substitution with Aqueous Solutions of Nucleophiles. Journal of the American Chemical Society 2019, 141
(31)
, 12212-12218. https://doi.org/10.1021/jacs.9b05830
- Adrien Quintard, Céline Sperandio, Jean Rodriguez. Modular Enantioselective Synthesis of an Advanced Pentahydroxy Intermediate of Antimalarial Bastimolide A and of Fluorinated and Chlorinated Analogues. Organic Letters 2018, 20
(17)
, 5274-5277. https://doi.org/10.1021/acs.orglett.8b02213
- Desta
Doro Bume, Stefan Andrew Harry, Thomas Lectka, Cody Ross Pitts. Catalyzed and Promoted Aliphatic Fluorination. The Journal of Organic Chemistry 2018, 83
(16)
, 8803-8814. https://doi.org/10.1021/acs.joc.8b00982
- Julius Adam V. Lopez, Julie G. Petitbois, Charles S. Vairappan, Taiki Umezawa, Fuyuhiko Matsuda, and Tatsufumi Okino . Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia. Organic Letters 2017, 19
(16)
, 4231-4234. https://doi.org/10.1021/acs.orglett.7b01869
- Haoxuan Wang, Jeffrey C. Yang, and Stephen L. Buchwald . CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines. Journal of the American Chemical Society 2017, 139
(25)
, 8428-8431. https://doi.org/10.1021/jacs.7b04816
- Nikolaos Kaplaneris, Constantinos Spyropoulos, Maroula G. Kokotou, and Christoforos G. Kokotos . Enantioselective Organocatalytic Synthesis of 2-Oxopiperazines from Aldehydes: Identification of the Elusive Epoxy Lactone Intermediate. Organic Letters 2016, 18
(22)
, 5800-5803. https://doi.org/10.1021/acs.orglett.6b02699
- David A. Petrone, Juntao Ye, and Mark Lautens . Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation. Chemical Reviews 2016, 116
(14)
, 8003-8104. https://doi.org/10.1021/acs.chemrev.6b00089
- Alejandro M. Fracaroli, Peter Siman, David A. Nagib, Mitsuharu Suzuki, Hiroyasu Furukawa, F. Dean Toste, and Omar M. Yaghi . Seven Post-synthetic Covalent Reactions in Tandem Leading to Enzyme-like Complexity within Metal–Organic Framework Crystals. Journal of the American Chemical Society 2016, 138
(27)
, 8352-8355. https://doi.org/10.1021/jacs.6b04204
- Shashikant U. Dighe, Rohit Mahar, Sanjeev K. Shukla, Ruchir Kant, Kumkum Srivastava, and Sanjay Batra . Synthesis of S-(−)-5,6-Dihydrocanthin-4-ones via a Triple Cooperative Catalysis-Mediated Domino Reaction. The Journal of Organic Chemistry 2016, 81
(11)
, 4751-4761. https://doi.org/10.1021/acs.joc.6b00613
- Jordi Burés, Alan Armstrong, and Donna G. Blackmond . Explaining Anomalies in Enamine Catalysis: “Downstream Species” as a New Paradigm for Stereocontrol. Accounts of Chemical Research 2016, 49
(2)
, 214-222. https://doi.org/10.1021/acs.accounts.5b00394
- Ciril Jimeno, Lidong Cao, and Philippe Renaud . Trichloromethanesulfonyl Chloride: A Chlorinating Reagent for Aldehydes. The Journal of Organic Chemistry 2016, 81
(3)
, 1251-1255. https://doi.org/10.1021/acs.joc.5b02543
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(18)
, 4596-4599. https://doi.org/10.1021/acs.orglett.5b02323
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(34)
, 10852-10866. https://doi.org/10.1021/jacs.5b05841
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(15)
, 3868-3871. https://doi.org/10.1021/acs.orglett.5b01844
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(44)
, 15775-15780. https://doi.org/10.1021/ja509236u
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(16)
, 7881-7929. https://doi.org/10.1021/cr400553c
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(3)
, 976-983. https://doi.org/10.1021/jo402422b
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(24)
, 12809-12813. https://doi.org/10.1021/jo402220s
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(23)
, 11948-11955. https://doi.org/10.1021/jo401996m
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(16)
, 8208-8213. https://doi.org/10.1021/jo4013223
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(16)
, 8074-8082. https://doi.org/10.1021/jo401345m
- 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
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(8)
, 1914-1917. https://doi.org/10.1021/ol400566j
- Aurélien Alix, Claudia Lalli, Pascal Retailleau, and Géraldine Masson . Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts. Journal of the American Chemical Society 2012, 134
(25)
, 10389-10392. https://doi.org/10.1021/ja304095z
- 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
- Margaret L. Wong, Ilia A. Guzei, and Laura L. Kiessling . An Asymmetric Synthesis of l-Pyrrolysine. Organic Letters 2012, 14
(6)
, 1378-1381. https://doi.org/10.1021/ol300045c
- Feng Li, Jing Nie, Jun-Wei Wu, Yan Zheng, and Jun-An Ma . Stereoselective Synthesis of Fluorinated 2,3-Dihydroquinolin-4(1H)-ones via a One-Pot Multistep Transformation. The Journal of Organic Chemistry 2012, 77
(5)
, 2398-2406. https://doi.org/10.1021/jo202693x
- Jakub Saadi, Matsujiro Akakura, and Hisashi Yamamoto . Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes. Journal of the American Chemical Society 2011, 133
(36)
, 14248-14251. https://doi.org/10.1021/ja2066169
- Albert Moyano and Ramon Rios . Asymmetric Organocatalytic Cyclization and Cycloaddition Reactions. Chemical Reviews 2011, 111
(8)
, 4703-4832. https://doi.org/10.1021/cr100348t
- K. C. Nicolaou, Nicholas L. Simmons, Yongcheng Ying, Philipp M. Heretsch, and Jason S. Chen . Enantioselective Dichlorination of Allylic Alcohols. Journal of the American Chemical Society 2011, 133
(21)
, 8134-8137. https://doi.org/10.1021/ja202555m
- Wenhua Zheng, Zuhui Zhang, Matthew J. Kaplan, and Jon C. Antilla . Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles. Journal of the American Chemical Society 2011, 133
(10)
, 3339-3341. https://doi.org/10.1021/ja109824x
- Jason A. Witek and Steven M. Weinreb . Investigation of the Stereochemistry of Intermolecular Conjugate Additions of Nucleophiles to Acyclic Nitrosoalkenes. Organic Letters 2011, 13
(5)
, 1258-1260. https://doi.org/10.1021/ol2000793
- Ross M. Denton, Xiaoping Tang, and Adam Przeslak. Catalysis of Phosphorus(V)-Mediated Transformations: Dichlorination Reactions of Epoxides Under Appel Conditions. Organic Letters 2010, 12
(20)
, 4678-4681. https://doi.org/10.1021/ol102010h
- Jason A. Draper and Robert Britton. A Concise and Stereoselective Synthesis of Hydroxypyrrolidines: Rapid Synthesis of (+)-Preussin. Organic Letters 2010, 12
(18)
, 4034-4037. https://doi.org/10.1021/ol101631e
- Stijn Dekeukeleire, Matthias D’hooghe, Karl W. Törnroos and Norbert De Kimpe . Stereoselective Synthesis of Chiral 4-(1-Chloroalkyl)-β-Lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines. The Journal of Organic Chemistry 2010, 75
(17)
, 5934-5940. https://doi.org/10.1021/jo101220q
- Olugbeminiyi O. Fadeyi, Michael L. Schulte and Craig W. Lindsley. General Access to Chiral N-Alkyl Terminal Aziridines via Organocatalysis. Organic Letters 2010, 12
(14)
, 3276-3278. https://doi.org/10.1021/ol101276x
- Xin-Hua Duan and Herbert Mayr. Electrophilicities of α-Chlorinating Agents Used in Organocatalysis. Organic Letters 2010, 12
(10)
, 2238-2241. https://doi.org/10.1021/ol100592j
- Baldip Kang, Stanley Chang, Shannon Decker and Robert Britton. Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans. Organic Letters 2010, 12
(8)
, 1716-1719. https://doi.org/10.1021/ol100260z
- Anna E. Allen and David W. C. MacMillan. The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes. Journal of the American Chemical Society 2010, 132
(14)
, 4986-4987. https://doi.org/10.1021/ja100748y
- Harit U. Vora and Tomislav Rovis. N-Heterocyclic Carbene Catalyzed Asymmetric Hydration: Direct Synthesis of α-Protio and α-Deuterio α-Chloro and α-Fluoro Carboxylic Acids. Journal of the American Chemical Society 2010, 132
(9)
, 2860-2861. https://doi.org/10.1021/ja910281s
- Shoji Kobayashi, Tatsuhiro Kinoshita, Hisatoshi Uehara, Tomoko Sudo and Ilhyong Ryu. Organocatalytic Enantioselective Synthesis of Nitrogen-Substituted Dihydropyran-2-ones, a Key Synthetic Intermediate of 1β-Methylcarbapenems. Organic Letters 2009, 11
(17)
, 3934-3937. https://doi.org/10.1021/ol901544q
- Baldip Kang, Jeffrey Mowat, Thomas Pinter and Robert Britton. Development of a Concise and General Enantioselective Approach to 2,5-Disubstituted-3-hydroxytetrahydrofurans. Organic Letters 2009, 11
(8)
, 1717-1720. https://doi.org/10.1021/ol802711s
- Kimberly S. Petersen and Gary H. Posner. Asymmetric, Organocatalytic, Three-Step Synthesis of γ-Hydroxy-(E)-α,β-Unsaturated Sulfones and Esters. Organic Letters 2008, 10
(20)
, 4685-4687. https://doi.org/10.1021/ol8020513
- Grant M. Shibuya, Jacob S. Kanady and Christopher D. Vanderwal. Stereoselective Dichlorination of Allylic Alcohol Derivatives to Access Key Stereochemical Arrays of the Chlorosulfolipids. Journal of the American Chemical Society 2008, 130
(37)
, 12514-12518. https://doi.org/10.1021/ja804167v
- Taichi Kano,, Mitsuhiro Ueda, and, Keiji Maruoka. Direct Asymmetric Iodination of Aldehydes Using an Axially Chiral Bifunctional Amino Alcohol Catalyst. Journal of the American Chemical Society 2008, 130
(12)
, 3728-3729. https://doi.org/10.1021/ja074003o
- 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
- Baldip Kang and, Robert Britton. A General Method for the Synthesis of Nonracemic trans-Epoxides: Concise Syntheses of trans-Epoxide-Containing Insect Sex Pheromones. Organic Letters 2007, 9
(24)
, 5083-5086. https://doi.org/10.1021/ol702273n
- Yujiro Hayashi,, Hiromi Sekizawa,, Junichiro Yamaguchi, and, Hiroaki Gotoh. Organocatalyst-Mediated Enantioselective Intramolecular Aldol Reaction Featuring the Rare Combination of Aldehyde as Nucleophile and Ketone as Electrophile. The Journal of Organic Chemistry 2007, 72
(17)
, 6493-6499. https://doi.org/10.1021/jo0709100
- Saumen Hajra,, Manishabrata Bhowmick,, Biswajit Maji, and, Debarshi Sinha. Design and Synthesis of Chiral N-Chloroimidodicarbonates: Application to Asymmetric Chlorination of Silyl Enol Ethers. The Journal of Organic Chemistry 2007, 72
(13)
, 4872-4876. https://doi.org/10.1021/jo070614n
- Mattias Engman,, Jarle S. Diesen,, Alexander Paptchikhine, and, Pher G. Andersson. Iridium-Catalyzed Asymmetric Hydrogenation of Fluorinated Olefins Using N,P-Ligands: A Struggle with Hydrogenolysis and Selectivity. Journal of the American Chemical Society 2007, 129
(15)
, 4536-4537. https://doi.org/10.1021/ja0686763
- Ming He,, Gerson J. Uc, and, Jeffrey W. Bode. Chiral N-Heterocyclic Carbene Catalyzed, Enantioselective Oxodiene Diels−Alder Reactions with Low Catalyst Loadings. Journal of the American Chemical Society 2006, 128
(47)
, 15088-15089. https://doi.org/10.1021/ja066380r
- Naidu S. Chowdari,, Moballigh Ahmad,, Klaus Albertshofer,, Fujie Tanaka, and, Carlos F. Barbas, III. Expedient Synthesis of Chiral 1,2- and 1,4-Diamines: Protecting Group Dependent Regioselectivity in Direct Organocatalytic Asymmetric Mannich Reactions. Organic Letters 2006, 8
(13)
, 2839-2842. https://doi.org/10.1021/ol060980d
- 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
- Timothy J. Peelen,, Yonggui Chi, and, Samuel H. Gellman. Enantioselective Organocatalytic Michael Additions of Aldehydes to Enones with Imidazolidinones: Cocatalyst Effects and Evidence for an Enamine Intermediate. Journal of the American Chemical Society 2005, 127
(33)
, 11598-11599. https://doi.org/10.1021/ja0532584
- Teresa D. Beeson and, David W. C. MacMillan. Enantioselective Organocatalytic α-Fluorination of Aldehydes. Journal of the American Chemical Society 2005, 127
(24)
, 8826-8828. https://doi.org/10.1021/ja051805f
- Naidu S. Chowdari and, Carlos F. Barbas, III. Total Synthesis of LFA-1 Antagonist BIRT-377 via Organocatalytic Asymmetric Construction of a Quaternary Stereocenter. Organic Letters 2005, 7
(5)
, 867-870. https://doi.org/10.1021/ol047368b
- Maria Rosaria Acocella,, Olga García Mancheño,, Marco Bella, and, Karl Anker Jørgensen. Organocatalytic Asymmetric Hydroxylation of β-Keto Esters: Metal-Free Synthesis of Optically Active anti-Diols. The Journal of Organic Chemistry 2004, 69
(23)
, 8165-8167. https://doi.org/10.1021/jo048655w
- Rajeswari Thayumanavan,, Fujie Tanaka, and, Carlos F. Barbas III. Direct Organocatalytic Asymmetric Aldol Reactions of α-Amino Aldehydes: Expedient Syntheses of Highly Enantiomerically Enriched anti-β-Hydroxy-α-amino Acids. Organic Letters 2004, 6
(20)
, 3541-3544. https://doi.org/10.1021/ol0485417
- Naidu S. Chowdari,, Jeff T. Suri, and, Carlos F. Barbas III. Asymmetric Synthesis of Quaternary α- and β-Amino Acids and β-Lactams via Proline-Catalyzed Mannich Reactions with Branched Aldehyde Donors. Organic Letters 2004, 6
(15)
, 2507-2510. https://doi.org/10.1021/ol049248+
- Navjeet Kaur. Synthesis of aziridines from enamines and haloamines. 2026, 179-213. https://doi.org/10.1016/B978-0-443-44508-8.00007-9
- Bingxing Zhou, Lei Bai, Changming Xu. Active electropositive α-chlorine: trichloroacetonitrile as an electrophilic chlorination reagent. Organic Chemistry Frontiers 2025, 12
(19)
, 5211-5217. https://doi.org/10.1039/D5QO00379B
- Taiki Umezawa. Synthetic Study on Mytilipin C and Development of New Synthetic Methodology toward Total Synthesis. Journal of Synthetic Organic Chemistry, Japan 2025, 83
(7)
, 651-662. https://doi.org/10.5059/yukigoseikyokaishi.83.651
- Ramon Arora, Philip Samokhin, Mark Lautens. Photoexcited Transition‐Metal Catalyzed Carbon‐Halogen Bond Formation. Angewandte Chemie 2025, 137
(15)
https://doi.org/10.1002/ange.202500929
- Ramon Arora, Philip Samokhin, Mark Lautens. Photoexcited Transition‐Metal Catalyzed Carbon‐Halogen Bond Formation. Angewandte Chemie International Edition 2025, 64
(15)
https://doi.org/10.1002/anie.202500929
- Xue Du, Ze-Hua Sun, Penglei Zhang, Li Ping Xu, Xiaodong Xiong. Asymmetric chloro- and selenocyclization of 2-alkenyl anilides enabled by tertiary ammonium salt catalysis. Chinese Chemical Letters 2025, 48 , 111259. https://doi.org/10.1016/j.cclet.2025.111259
- Navjeet Kaur. Synthesis of azetidines from amine moiety bearing compounds-II. 2025, 31-54. https://doi.org/10.1016/B978-0-443-27684-2.00010-8
- Stefano Andolina, Alessandra Puglisi, Sergio Rossi, Fabrizio Medici, Maurizio Benaglia. Enantioselective organocatalytic electrochemical α-chlorination of aldehydes. Organic Chemistry Frontiers 2025, 126 S1 https://doi.org/10.1039/D5QO01249J
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(5)
https://doi.org/10.1177/1934578X241250236
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(20)
https://doi.org/10.1002/chem.202304289
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(1)
https://doi.org/10.1038/s41467-023-37346-7
- Guo Liu, Pingfan Li. Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide. Synlett 2023, 34
(20)
, 2447-2450. https://doi.org/10.1055/a-2088-9219
- Kazutaka Shibatomi. Organocatalytic Synthesis of Chiral Halogenated Compounds. The Chemical Record 2023, 23
(7)
https://doi.org/10.1002/tcr.202300061
- Jordi Burés, Alan Armstrong, Donna G. Blackmond. A Tutorial on
Kinetic‐Assisted
Mechanistic Analysis in Asymmetric Aminocatalysis. 2023, 657-678. https://doi.org/10.1002/9783527832217.ch20
- Yao Tang, Yu Wang, Qingkai Yuan, Sai Zhang, Jia-Yin Wang, Shengzhou Jin, Ting Xu, Junyi Pan, Kazimierz Surowiec, Guigen Li. Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates. Research 2023, 6 https://doi.org/10.34133/research.0163
- Md. Wali Ullah, Naoki Haraguchi. Asymmetric Diels‐Alder Reaction Catalyzed by Facile Recoverable Ionically Core‐Corona Polymer Microsphere‐Immobilized MacMillan Catalyst. ChemistrySelect 2022, 7
(37)
https://doi.org/10.1002/slct.202202568
- Yujiro Hayashi. ASYMMETRIC ENAMINE AND IMINIUM ION CATALYSIS. 2022, 1-28. https://doi.org/10.1002/9781119736424.ch1
- Wenhua Ou, Ruolin Wang, Ruonan Liu, Hong Huang. An Improved and Suitable Method for Large Scale Production of
α-Monochlorocyclodecanone. Letters in Organic Chemistry 2022, 19
(5)
, 418-421. https://doi.org/10.2174/1570178618666210217121023
- Nick Wannenmacher, Noah Keim, Wolfgang Frey, René Peters. Catalytic Asymmetric Chlorination of Isoxazolinones. European Journal of Organic Chemistry 2022, 2022
(9)
https://doi.org/10.1002/ejoc.202200030
- Jiahang Yan, Zhiqiang Zhou, Qiaoqiao He, Guzhou Chen, Hongbo Wei, Weiqing Xie. The applications of catalytic asymmetric halocyclization in natural product synthesis. Organic Chemistry Frontiers 2022, 9
(2)
, 499-516. https://doi.org/10.1039/D1QO01395E
- Michael Meanwell, Gaelen Fehr, Weiwu Ren, Bharanishashank Adluri, Victoria Rose, Johannes Lehmann, Steven M. Silverman, Rozhin Rowshanpour, Christopher Adamson, Milan Bergeron-Brlek, Hayden Foy, Venugopal Rao Challa, Louis-Charles Campeau, Travis Dudding, Robert Britton. Diversity-oriented synthesis of glycomimetics. Communications Chemistry 2021, 4
(1)
https://doi.org/10.1038/s42004-021-00520-3
- Lu Xiao, Liang Wei, Chun‐Jiang Wang. Stereodivergent Synthesis of Enantioenriched γ‐Butyrolactones Bearing Two Vicinal Stereocenters Enabled by Synergistic Copper and Iridium Catalysis. Angewandte Chemie 2021, 133
(47)
, 25134-25144. https://doi.org/10.1002/ange.202107418
- Lu Xiao, Liang Wei, Chun‐Jiang Wang. Stereodivergent Synthesis of Enantioenriched γ‐Butyrolactones Bearing Two Vicinal Stereocenters Enabled by Synergistic Copper and Iridium Catalysis. Angewandte Chemie International Edition 2021, 60
(47)
, 24930-24940. https://doi.org/10.1002/anie.202107418
- Woong-Sup Lee, Linzi Li, Byeong Moon Kim. SuFEx-Click Approach for the Synthesis of Soluble Polymer-Bound MacMillan Catalysts for the Asymmetric Diels–Alder Reaction. Catalysts 2021, 11
(9)
, 1044. https://doi.org/10.3390/catal11091044
- Philip J. Chevis, Stephen G. Pyne. Synthesis of enantioenriched α-heteroatom functionalised aldehydes by chiral organocatalysis and their synthetic applications. Organic Chemistry Frontiers 2021, 8
(10)
, 2287-2314. https://doi.org/10.1039/D1QO00101A
- Adrien Quintard. Development of Multi‐Catalytic Strategies Based on the Combination between Iron‐/Copper‐ and Organo‐Catalysis. Israel Journal of Chemistry 2021, 61
(5-6)
, 278-288. https://doi.org/10.1002/ijch.202000018
- Venugopal Rao Challa, Daniel Kwon, Matthew Taron, Hope Fan, Baldip Kang, Darryl Wilson, F. P. Jake Haeckl, Sandra Keerthisinghe, Roger G. Linington, Robert Britton. Total synthesis of biselide A. Chemical Science 2021, 12
(15)
, 5534-5543. https://doi.org/10.1039/D0SC06223E
- K. Ben Ali. Asymmetric Epoxidation of Unfunctionalized Olefins Using Novel Chiral Dihydroisoquinolinium Salts as Organocatalysts. Russian Journal of Organic Chemistry 2021, 57
(4)
, 638-646. https://doi.org/10.1134/S1070428021040205
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