A stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

被引：35

作者：

Hoang, Cam Thuy ^{[1
]}

Alezra, Valerie ^{[1
]}

Guillot, Regis ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, UMR CNRS 8182, Lab Chim Procedes & Substances Nat, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 13期

关键词：

D O I：

10.1021/ol0708020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, stereoselective synthesis of 4,5-disubstituted imidazolidines-2-ones from alpha-aminoacids has been developed: the key steps are a Blaise reaction of bromoacetate on alpha-aminonitriles and further reduction. Although reduction with sodium cyanoborohydride afforded a mixture of cis and trans isomers 6a-e with moderate to good stereoselectivity, reduction with sodium in liquid ammonia gave the trans isomers 8a-e with complete stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to beta,gamma-diaminoacids or 3-aminopyrrolidines.

引用

页码：2521 / 2524

页数：4

共 22 条

[1]

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[2]

CAINE D, 1976, ORG REACTIONS, V23, P1

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