Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-Sulfonylimines mediated by hydrogen

被引：30

作者：

Garner, Susan A. ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

D O I：

10.1021/jo070779w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of N-(o-nitrophenylsulfonyl)imines 8a-13a at ambient pressure with tri-2-furylphosphine-ligated rhodium catalysts enables formation of Mannich products 8b-13b and 8c-13c with moderate to good levels of syn-diastereoselectivity. As revealed by an assay of various N-protecting groups, excellent yields of reductive Mannich product also are obtained for N-arylimines 1a-4a, although diminished levels of syn-diastereoselectivity are observed. Coupling of MVK to imine 8a under a deuterium atmosphere provides deuterio-8b, which incorporates a single deuterium atom at the former enone beta-position.

引用

页码：5843 / 5846

页数：4

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