Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols

被引：7
|
作者：
Fordred, Paul S. [1 ]
Bull, Steven D. [1 ]
机构：
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 01期
基金：
英国工程与自然科学研究理事会;
关键词：
Hydroboration; Reduction; beta; gamma-Unsaturated ester; Chiral 1,3-diol; IpcBH(2); HYDROBORATING AGENT; ENANTIOMERIC PURITY; NMR ANALYSIS; MONOISOPINOCAMPHEYLBORANE; REDUCTION; ALKENES; OLEFINS; KETONES; DIOLS;
D O I：
10.1016/j.tetlet.2012.10.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of a range of trisubstituted beta,gamma-unsaturated esters with 2 equiv of (-)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal beta,gamma-(anti)-stereocentres in 67-85% enantiomeric excess. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：27 / 31
页数：5
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