CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY CATECHOLBORANE

被引：114

作者：

EVANS, DA

FU, GC

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 22期

关键词：

D O I：

10.1021/jo00309a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: α,β-Unsaturated ketones which can readily adopt an s-cis conformation undergo conjugate reduction by catecholborane at room temperature. α,β-Unsaturated imides, esters, and amides are unreactive under the same conditions. However, catalytic quantities of Rh(PPh3)3C1 greatly accelerate the 1,4-addition process, effecting conjugate reduction of these substrates by catecholborane at -20 °C. The resulting boron enolates may be reacted with electrophiles to provide functionalized products. © 1990, American Chemical Society. All rights reserved.

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页码：5678 / 5680

页数：3

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