Sequential reactions promoted by manganese:: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids

被引：33

作者：

Concellon, Jose M. ^{[1
]}

Rodriguez-Solla, Humberto ^{[1
]}

Diaz, Pamela ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 21期

关键词：

D O I：

10.1021/jo701417z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A complete E-selective synthesis of a,alpha,beta-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes promoted by Rieke manganese (Mn*) is reported. A mechanism based on a sequential aldol-type reaction and a completely stereoselective beta-elimination is proposed to explain these results. The unsaturated amides obtained are readily and efficiently transformed into alpha,beta-unsaturated ketones, aldehydes, or carboxylic acids without loss of the diastereoisomeric purity of the C-C double bond.

引用

页码：7974 / 7979

页数：6

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