Chiral N-phosphonyl imine chemistry: asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

被引：15

作者：

Ai Teng ^{[1
]}

Pindi, Suresh ^{[1
]}

Kattamuri, Padmanabha V. ^{[1
]}

Li GuiGen ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

SCIENCE CHINA-CHEMISTRY | 2010年 / 53卷 / 01期

基金：

美国国家卫生研究院;

关键词：

chiral N-phosphonyl imine; chiral phosphoramide; glycine enolate; alpha-beta diamino ester; BETA-AMINO; ALPHA; BETA-DIAMINO ACIDS; MANNICH REACTION; ESTERS; DERIVATIVES; AZIRIDINIUM; COMPLEXES; SERINE;

D O I：

10.1007/s11426-010-0026-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diphenyl diamine-based phosphonyl imines attached by the N-isopropyl group in the auxiliary have been synthesized in good yields under convenient reaction conditions. These new chiral N-phosphonyl imines can react with glycine enolate smoothly to give chiral alpha-beta diamino esters in good yields (72%-90%) and up to excellent diastereoselectivity (>99:1 dr). By treatment with HBr, the chiral auxiliary can be readily removed. The absolute structure has been unambiguously determined by converting a product to a known sample.

引用

页码：125 / 129

页数：5

共 37 条

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