A versatile route to syn- and anti-α-amino β-hydroxy esters from β-keto esters by dynamic kinetic resolution with Ru-SYNPHOS® catalyst

被引：0

作者：

Mordant, C ^{[1
]}

Dünkelmann, P ^{[1
]}

Ratovelomanana-Vidal, V ^{[1
]}

Genet, JP ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, CNRS, UMR 7573, Lab Synthese Select Organ & Prod Nat, F-75231 Paris 05, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 14期

关键词：

alpha-amino-beta-hydroxy esters; asymmetric hydrogenation; catalysis; dynamic kinetic resolution; ruthenium;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and practical synthesis of both syn- and anti-alpha-amino beta-hydroxy esters with high levels of selectivity by the use of Ru-SYNPHOS(R) catalysts is reported. The key transformations include asymmetric hydrogenations of alpha-N-substituted beta-keto esters protected as alpha-amido or alpha-amino hydrochloride derivatives, respectively. The Ru-II-catalyzed hydrogenation of alpha-amino beta-keto ester hydrochlorides affords the corresponding anti-alpha-amino beta-hydroxy esters with high diastereoselectivities (up to 99%) and enantioselectivities (up to 97%) through dynamic kinetic resolution (DKR). ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：3017 / 3026

页数：10

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