Asymmetric hydrogenation of alpha-keto acid derivatives by rhodium-{amidophosphine-phosphinite} catalysts

被引：86

作者：

Carpentier, JF

Mortreux, A

机构：

[1] Grp. de Chim. Organ. Appl., Associé au CNRS, Ecl. Natl. Sup. de Chimie de Lille, 59652 Villeneuve d'Ascq

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(97)00078-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective hydrogenation of several alpha-keto esters (3a-f, 5a-j), alpha-keto amides (7a-e) and isatine derivatives (9a-d) with a set of four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetato-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis of aliphatic oc-hydroxy esters 4a-f in moderate to high enantioselectivities (66-95% ee), in contrast to most aromatic alpha-hydroxy esters 6a-j (8-81% ee). Best enantioselectivities for alpha-hydroxy amides 8a-e (85-95% ee) and dioxindoles 10a-d (80-94% ee) were obtained with chloro-Rh-AMPP precursors. It is proposed that, contrary to alpha-keto amides, alpha-keto esters do not chelate onto the rhodium center and that, in such circumstances, the asymmetric induction is mainly controlled by the steric hindrance around the C=O function. (C) 1997 Elsevier Science Ltd.

引用

页码：1083 / 1099

页数：17

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