Catalytic anti-Selective Asymmetric Hydrogenation of α-Amino-β-Keto Esters through Dynamic Kinetic Resolution

被引：13

作者：

Hamada, Yasumasa ^{[1
]}

Makino, Kazuishi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Yayoi, Chiba 2638522, Japan

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2008年 / 66卷 / 11期

关键词：

D O I：

10.5059/yukigoseikyokaishi.66.1057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru), rhodium (Rh), and iridium (1r)-chiral phosphine catalysts proceeds anti-selectively through dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purity, which are important intermediates for the synthesis of medicines and natural products. The mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place through the hydrogenation of the double bond in the enol tautomer of the substrate and the Rh- and Ir-catalyzed asymmetric hydrogenations proceed through the reduction of the keto tautomer of the substrate.

引用

页码：1057 / 1065

页数：9

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