Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids

被引：109

作者：

Burk, MJ ^{[1
]}

Allen, JG ^{[1
]}

Kiesman, WF ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27708 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 04期

关键词：

D O I：

10.1021/ja9731074

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An extremely efficient method has been found for the catalytic asymmetric hydrogenation of conjugated alpha,gamma-dienamide esters using the Et-DuPHOS-Rh catalyst system. alpha,gamma-Dienamide ester substrates were prepared via the Suzuki cross-coupling reaction and the Horner-Emmons olefination. Full conversion to the corresponding gamma,delta-unsaturated amino acids with very high regio-and enantioselectivity was achieved after short reaction times. This new methodology was applied to the synthesis of the natural product bulgecinine from a prochiral dienamide ester.

引用

页码：657 / 663

页数：7

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