Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols with three contiguous stereocenters

被引：62

作者：

Lurain, AE ^{[1
]}

Maestri, A ^{[1
]}

Kelly, AR ^{[1
]}

Carroll, PJ ^{[1
]}

Walsh, PJ ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 42期

关键词：

D O I：

10.1021/ja046750g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols with up to three contiguous stereocenters are reported. Route one involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective epoxidation. Route two entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective epoxidation. The oxidant for the epoxidation is generated by exposure of the allylic alkoxide intermediate and the remaining organozinc reagent to dioxygen. Upon addition of catalytic titanium tetraisopropoxide, the directed epoxidation yields the epoxy alcohols with good to excellent yields. Copyright © 2004 American Chemical Society.

引用

页码：13608 / 13609

页数：2

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