Chiral N-phosphonyl imine chemistry:: Asymmetric additions of ester enolates for the synthesis of β-amino acids

被引：35

作者：

Han, Jianlin ^{[1
]}

Ai, Teng ^{[1
]}

Nguyen, Thao ^{[1
]}

Li, Guigen ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79401 USA

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2008年 / 72卷 / 02期

基金：

美国国家卫生研究院;

关键词：

chiral N-phosphonyl imines; chiral phospheramide; lithium enolate; triisopropoxytitanium(IV) chloride; beta-amino acid;

D O I：

10.1111/j.1747-0285.2008.00682.x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Chiral phosphonl imines attached by 1-naphthyl protection group were found to react with lithium ester enolates smoothly and give chiral beta-amino esters in good yields (70-88%) and up to excellent diastereoselectivity (> 99:1 dr). Triisopropoxytitanium (IV) chloride was found to enhance diastereoseletivity when used as the Lewis acid promoter. The chiral auxiliary can be readily removed by treating with HBr to give free amino esters. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample. This reaction provides an easy access to beta-amino acid derivatives.

引用

页码：120 / 126

页数：7

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