A class of ruthenium(II) catalyst for asymmetric transfer hydrogenations of ketones

被引：257

作者：

Hayes, AM

Morris, DJ

Clarkson, GJ

Wills, M ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Asymetr Catalysis Grp, Coventry CV4 7AL, W Midlands, England

[2] Univ Warwick, Dept Chem, Xray Crystallog Unit, Coventry CV4 7AL, W Midlands, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/ja051486s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ruthenium dimer 6 (readily available in two steps from TsDPEN) is converted directly to monomeric asymmetric transfer hydrogenation catalyst 3 in situ under the conditions employed for ketone reduction. Catalyst 3 is a significantly more active catalyst for this application than the untethered derivative, exhibits higher enantioselectivities across a range of substrates, and appears to be highly stable to the reaction conditions. It is active at loadings of as low as 0.01 mol %, and reductions at the 0.1 mol % level are complete within 20 min at 80 °C without significant loss of enantioselectivity. Copyright © 2005 American Chemical Society.

引用

收藏

页码：7318 / 7319

页数：2

相关论文

共 40 条

[1] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using chiral oxazolinylferrocenylphosphines and one of their Ru(II) complex [J].

Arikawa, Y ;

Ueoka, M ;

Matoba, K ;

Nishibayashi, Y ;

Hidai, M ;

Uemura, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 572 (02) :163-168

[2] A soluble-polymer system for the asymmetric transfer hydrogenation of ketones [J].

Bastin, S ;

Eaves, RJ ;

Edwards, CW ;

Ichihara, O ;

Whittaker, M ;

Wills, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5405-5412

[3] Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones [J].

Brandt, P ;

Roth, P ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4885-4890

[4] Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation [J].

Bubert, C ;

Blacker, J ;

Brown, SM ;

Crosby, J ;

Fitzjohn, S ;

Muxworthy, JP ;

Thorpe, T ;

Williams, JMJ .

TETRAHEDRON LETTERS, 2001, 42 (24) :4037-4039

[5] Asymmetric transfer hydrogenation of aromatic ketones catalyzed by the iridium hydride complex under ambient conditions [J].

Chen, JS ;

Li, YY ;

Dong, ZR ;

Li, BZ ;

Gao, JX .

TETRAHEDRON LETTERS, 2004, 45 (45) :8415-8418

[6] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].

Clapham, SE ;

Hadzovic, A ;

Morris, RH .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237

[7] Rutheuium(II)-catalyzed asymmetric transfer hydrogenation of carbonyl compounds with 2-propanol and ephedrine-type ligands [J].

Everaere, K ;

Mortreux, A ;

Carpentier, JF .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :67-77

[8] A general strategy for improving enantiomeric purities via the tandem use of mirror-image catalysts [J].

Faller, JW ;

Lavoie, AR .

ORGANOMETALLICS, 2002, 21 (09) :2010-2012

[9] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].

Fujii, A ;

Hashiguchi, S ;

Uematsu, N ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522

[10] The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].

Haack, KJ ;

Hashiguchi, S ;

Fujii, A ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288

← 1 2 3 4 →