Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions

被引：33

作者：

Singh, S ^{[1
]}

Han, H ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 33期

基金：

美国国家卫生研究院;

关键词：

polyhydroxylated pyrrolidines; regioselective asymmetric ammohydroxylation; allylic epoxidation; intramolecular cyclization;

D O I：

10.1016/j.tetlet.2004.06.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)(2)/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting 8-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6349 / 6352

页数：4

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