Acid-Catalyzed Highly Enantioselective Synthesis of α-Amino Acid Derivatives from Sulfinamides and Alkynes

被引：3

作者：

Liu, Herui ^{[1
]}

Sun, Guangwu ^{[1
]}

Zhang, Yuchao ^{[2
]}

Li, Yongxi ^{[1
]}

Dong, Baobiao ^{[1
]}

Gao, Bing ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

[2] Univ Chinese Acad Sci, Inst Basic Med, Canc IBMC Canc Hosp, Hangzhou 310022, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 08期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC HYDROGENATION; YNAMIDES;

D O I：

10.1021/acs.orglett.3c04158

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective difunctionalization of activated alkynes using chiral sulfinamide reagents is developed. It is an atom and chirality transfer process that allows for the modular synthesis of optically active alpha-amino acid derivatives under mild conditions. The reaction proceeds through an acid-catalyzed [2,3]-sigmatropic rearrangement mechanism with predictable stereochemistry and a broad scope.

引用

页码：1601 / 1606

页数：6

共 50 条

[1] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids
Córdova, A
Notz, W
Zhong, GF
Betancort, JM
Barbas, CF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1842 - 1843
[2] Asymmetric amplification in the amino acid-catalyzed synthesis of amino acid derivatives
Ibrahem, Ismail
Sunden, Henrik
Dziedzic, Pawel
Rios, Ramon
Cordova, Armando
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1868 - 1872
[3] Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Pyrazole-Based Unnatural α-Amino Acid Derivatives
Woldegiorgis, Alemayehu Gashaw
Han, Zhao
Lin, Xufeng
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 274 - 280
[4] Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes
Ibrahem, I
Córdova, A
TETRAHEDRON LETTERS, 2005, 46 (16) : 2839 - 2843
[5] Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction
Jousseaume, Thierry
Wurz, Nathalie E.
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1410 - 1414
[6] Highly Enantioselective Synthesis of β-Amino Acid Derivatives by the Lewis Base Catalyzed Hydrosilylation of β-Enamino Esters
Zheng, Hong-Jie
Chen, Wen-Bing
Wu, Zhi-Jun
Deng, Jin-Gen
Lin, Wen-Qing
Yuan, Wei-Cheng
Zhang, Xiao-Mei
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (32) : 9864 - 9867
[7] Highly enantioselective synthesis of α-amino acid derivatives by an NHC-catalyzed intermolecular Stetter reaction
Wurz, Nathalie E.
Jousseaume, Thierry
Schedler, Michael
Glorius, Frank
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[8] Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
Jiaping, Jin
Woldegiorgis, Alemayehu Gashaw
Lin, Xufeng
RSC ADVANCES, 2023, 13 (27) : 18964 - 18973
[9] Asymmetric amplification in the amino acid-catalyzed synthesis of amino acid derivatives (vol 349, pg 1868, 2007)
Ibrahem, I.
Sunden, H.
Dziedzic, P.
Rios, R.
Codova, A.
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) : 9 - 9
[10] Highly enantioselective synthesis of a fluorescent amino acid
Kele, P
Sui, GD
Huo, Q
Leblanc, RM
TETRAHEDRON-ASYMMETRY, 2000, 11 (24) : 4959 - 4963

← 1 2 3 4 5 →