Use of achiral (diphosphine)RuCl2(diamine) precatalysts as a practical alternative to sodium borohydride for ketone reduction

被引：25

作者：

de Koning, Pieter D. ^{[1
]}

Jackson, Mark ^{[1
]}

Lennon, Ian C. ^{[1
]}

机构：

[1] Chirotech Technol Ltd, Dowpharma, Cambridge CB4 0WG, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2006年 / 10卷 / 05期

关键词：

D O I：

10.1021/op060063n

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Stoichiometric sodium borohydride is frequently used in the chemoselective reduction of ketones to racemic secondary alcohols. Catalytic homogeneous hydrogenation using (diphosphine) RuCl2( diamine) complexes provides a practical and economic alternative. A range of substrates were investigated and the optimum precatalyst identified in each case. Norcamphor was reduced with high diastereoselectivity using (Ph3P)(2)RuCl2( en); (E)-4-phenylbut-3-en-2- one was reduced with good chemoselectivity, and acetophenone was hydrogenated very efficiently using the same precatalyst. Isophorone and 3-dimethylaminopropiophenone were effectively hydrogenated using (dppf) RuCl2(en).

引用

页码：1054 / 1058

页数：5

共 20 条

[1]

Aramini A, 2000, EUR J ORG CHEM, V2000, P1793

[2] LITHIUM TRI-SEC-BUTYLBOROHYDRIDE - NEW REAGENT FOR REDUCTION OF CYCLIC AND BICYCLIC KETONES WITH SUPER STEREOSELECTIVITY - REMARKABLY SIMPLE AND PRACTICAL PROCEDURE FOR CONVERSION OF KETONES TO ALCOHOLS IN EXCEPTIONALLY HIGH STEREOCHEMICAL PURITY [J].

BROWN, HC ;

KRISHNAMURTHY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7159-+

[3] PYRROLIDINES AND ALLYLIC AMINES FROM RADICAL-INDUCED CLEAVAGE OF AZIRIDINES [J].

DICKINSON, JM ;

MURPHY, JA .

TETRAHEDRON, 1992, 48 (07) :1317-1326

[4]

Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO

[5]

2-I

[6] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[7] ION-PAIR RETURN ASSOCIATED WITH SOLVOLYSIS OF ALPHA-PARA-ANISYLETHYL AND ALPHA-PHENYLETHYL PARA-NITROBENZOATES [J].

GOERING, HL ;

BRIODY, RG ;

SANDROCK, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (25) :7401-&

[8] Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst [J].

Hattori, K ;

Sajiki, H ;

Hirota, K .

TETRAHEDRON, 2001, 57 (23) :4817-4824

[9]

March J., 1992, ADV ORG CHEM, P910

[10]

MOLLOY BB, 1977, Patent No. 4018895

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