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
收藏
页码：6349 / 6352
页数：4
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