Synergistic Chiral Ion Pair Catalysts for Asymmetric Catalytic Synthesis of Quaternary α,β-Diamino Acids

被引：64

作者：

Shi, Shi-Hui ^{[1
]}

Huang, Fu-Ping ^{[1
]}

Zhu, Ping ^{[1
]}

Dong, Zhen-Wen ^{[1
]}

Hui, Xin-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 08期

关键词：

ALPHA-AMINO-ACIDS; TRANSITION-METAL CATALYSIS; DIRECT MANNICH REACTION; BRANCHED ENALS; SCHIFF-BASES; DERIVATIVES; IMINES; ESTERS; ORGANOCATALYSIS; CONSTRUCTION;

D O I：

10.1021/ol300510b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of a chiral phosphate anion with a silver ion has been demonstrated as a powerful and synergistic ion pair catalyst for the aza-Mannich reaction. A series of valuable quaternary alpha,beta-diamino acid derivatives was obtained in high yield, and with excellent diastereo- (up to 25:1 dr) and enantioselectivity (up to 99% ee). The adducts can be smoothly transformed into the corresponding protected chiral quaternary alpha,beta-diamino acids by a one-pot hydrolysis reaction.

引用

页码：2010 / 2013

页数：4

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