Facile Synthesis of Enantioenriched Cγ-Tetrasubstituted α-Amino Acid Derivatives via an Asymmetric Nucleophilic Addition/Protonation Cascade

被引：64

作者：

Duan, Shu-Wen ^{[1
]}

An, Jing ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; ENOLATE PROTONATIONS; 3+2 CYCLOADDITION; MICHAEL ADDITION; SULFUR YLIDES; OXINDOLES; CATALYSIS; ESTERS; THIOUREA; STEREOCENTERS;

D O I：

10.1021/ol200550y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric nucleophilic addition/protonation reaction of 3-substituted oxindoles and ethyl 2-phthalimidoacrylate has been described. This strategy can give direct access to C-gamma-tetrasubstituted alpha-amino acid derivatives bearing 1,3-nonadjacent stereocenters with up to 98% yield, 94:6 dr, and > 99% ee. Dual activation is proposed in the transition state, and the opposite enantiomers can be obtained simply by changing cinchonidine-derived catalyst to the cinchonine analogue.

引用

页码：2290 / 2293

页数：4

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