Stereoselective reduction of α-bromopenicillanates by tributylphosphine

被引：7

作者：

Ishiwata, A ^{[1
]}

Kotra, LP ^{[1
]}

Miyashita, K ^{[1
]}

Nagase, T ^{[1
]}

Mobashery, S ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol000185e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective reduction of 6-bromo-6-substituted penicillanate esters has been achieved by treatment with tributylphosphine to give B-substituted penicillanate esters, This reaction would appear to proceed through a phosphonium beta-lactam enolate species, followed by a diastereoselective protonation, This method has the advantage of being simple to carry out and it is mild, gives high diastereoselectivity, and should tolerate a number of functional groups in the substrates, Implications of these observations are discussed.

引用

页码：2889 / 2892

页数：4

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