Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral -Amino Acid
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- 作者：Norihiro Ikemoto ; David M. Tellers ; Spencer D. Dreher ; Jinchu Liu ; Angie Huang ; Nelo R. Rivera ; Eugenia Njolito ; Yi Hsiao ; J. Christopher McWilliams ; J. Michael Williams ; Joseph D. Armstrong ; III ; Yon
- 刊名：Journal of the American Chemical Society
- 出版年：2004
- 出版时间：March 17, 2004
- 年：2004
- 卷：126
- 期：10
- 页码：3048 - 3049
- 全文大小：50K
- 年卷期：v.126,no.10(March 17, 2004)
- ISSN：1520-5126
文摘
Pure (Z)-enamines readily prepared from 
-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral -aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.
-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral -aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.