Stereocontrolled sequential functionalization in acyclic systems by exploiting internal 1,2-asymmetric induction - Generation of symmetry-related polyamino alcohol motifs

被引：45

作者：

Hanessian, S

Wang, WG

Gai, YH

机构：

[1] Department of Chemistry, Université de Montréal, Montreal, Que. H3C 3J7, C.P. 6128, Succ. Centre-ville

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 42期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/0040-4039(96)01754-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of acyclic gamma-ureido alpha,beta-unsatunted esters with lithium dialkyl or diaryl cuprates leads to the corresponding beta,gamma-substituted esters with high syn-stereoselectivity. The potassium enolates of these compounds react with trisyl azide or the Davis oxaziridine reagent to give all syn-orientated alpha-azido esters, or alpha-hydroxy esters. Mitsunobu inversion with azide ion produces diastereomeric compounds. The products are excellent examples of functionalized diamines and amino alcohols which can also be made in an iterative manner. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7477 / 7480

页数：4

共 36 条

[1] A diastereoselective synthesis of (2S, 3R, 4S)-2-amino-1-cyclohexyl-6-methylheptane-3,4-diol, the Abbott aminodiol. [J].