Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides

被引：11

作者：

Zhao MengMeng ^{[1
]}

Li WanFang ^{[1
]}

Ma Xin ^{[1
]}

Fan WeiZheng ^{[1
]}

Tao XiaoMing ^{[1
]}

Li XiaoMing ^{[1
]}

Xie XiaoMin ^{[1
]}

Zhang ZhaoGuo ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2013年 / 56卷 / 03期

基金：

中国国家自然科学基金;

关键词：

asymmetric hydrogenation; alpha-keto Weinreb amides; CeCl3 center dot 7H(2)O; METHOXY-N-METHYLAMIDES; ASYMMETRIC HYDROGENATION; N; N-DIMETHOXY-N; N-DIMETHYLETHANEDIAMIDE; CECL3-CENTER-DOT-7H(2)O; CONVERSION; COMPLEXES; ALKOXY;

D O I：

10.1007/s11426-012-4790-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric hydrogenation of alpha-keto Weinreb amides has been realized with [Ru((S)-Sunphos)(benzene)Cl]Cl as the catalyst and CeCl3 center dot 7H(2)O as the additive. A series of enantiopure alpha-hydroxy Weinreb amides (up to 97% ee) have been obtained. Catalytic amount of CeCl3 center dot 7H(2)O is essential for the high reactivity and enantioselectivity and the ratio of CeCl3 center dot 7H(2)O to [Ru((S)-Sunphos)(benzene)Cl]Cl plays an important role in the hydrogenation reaction.

引用

页码：342 / 348

页数：7

共 36 条

[1] Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation [J].

Andrus, Merritt B. ;

Hicken, Erik J. ;

Stephens, Jeffrey C. ;

Bedke, D. Karl .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8651-8654

[2] Diastereodivergent aldol reactions of β-alkoxy ethyl ketones:: Modular access to (1,4)-syn and -anti polypropionates [J].

Arikan, Fatih ;

Li, Jun ;

Menche, Dirk .

ORGANIC LETTERS, 2008, 10 (16) :3521-3524

[3] Highly Enantioselective Benzoin Condensation Reactions Involving a Bifunctional Protic Pentafluorophenyl-Substituted Triazolium Precatalyst [J].

Baragwanath, Louise ;

Rose, Christopher A. ;

Zeitler, Kirsten ;

Connon, Stephen J. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :9214-9217

[4] Synthesis of 1-aza-cryptophycin 1, an unstable cryptophycin. An unusual skeletal rearrangement [J].

Barrow, RA ;

Moore, RE ;

Li, LH ;

Tius, MA .

TETRAHEDRON, 2000, 56 (21) :3339-3351

[5] New methodology for the synthesis of α,α-difluoroketones [J].

Biju, Purakkattle .

SYNTHETIC COMMUNICATIONS, 2008, 38 (12) :1940-1945

[6] A combined NMR, DFT, and X-ray investigations of some cinchona alkaloid O-ethers [J].

Busygin, Igor ;

Nieminen, Ville ;

Taskinen, Antti ;

Sinkkonen, Jari ;

Toukoniitty, Esa ;

Sillanpaa, Reijo ;

Murzin, Dmitry Yu. ;

Leino, Reko .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6559-6569

[7] Asymmetric hydrogenation of alpha-keto acid derivatives by rhodium-{amidophosphine-phosphinite} catalysts [J].

Carpentier, JF ;

Mortreux, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :1083-1099

[8]

CHAN YNC, 1990, J AM CHEM SOC, V112, P9400

[9] Enantioselective Aerobic Oxidation of α-Hydroxy-Ketones Catalyzed by Oxidovanadium(V) Methoxides Bearing Chiral, N-Salicylidene-tert-butylglycinates [J].

Chen, Chien-Tien ;

Kao, Jun-Qi ;

Salunke, Santosh B. ;

Lin, Ya-Hui .

ORGANIC LETTERS, 2011, 13 (01) :26-29

[10] BICHEP - RU COMPLEXES, HIGHLY EFFICIENT CATALYSTS FOR ASYMMETRIC HYDROGENATION OF CARBONYL-COMPOUNDS [J].

CHIBA, T ;

MIYASHITA, A ;

NOHIRA, H ;

TAKAYA, H .

TETRAHEDRON LETTERS, 1993, 34 (14) :2351-2354

← 1 2 3 4 →