Reduction of imines via titanium-catalyzed hydromagnesation

被引：12

作者：

Amin, SR ^{[1
]}

Crowe, WE ^{[1
]}

机构：

[1] EMORY UNIV,DEPT CHEM,ATLANTA,GA 30322

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 43期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01797-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have recently discovered that imines can be reduced to amines via a titanium catalyzed hydromagnesation reaction. These reactions employ n-BuMgCl (1.2 eq) as the stoichiometric reducing agent and Cp2TiCl2 (3-5 mol%) as a catalyst. Reactions are run under nitrogen at ambient temperature and pressure. For most aldimine and cyclic ketimine substrates amine products are obtained in yields ranging from 69-94%. The reaction is not tolerant of bulky nitrogen substituents or primary enolizable protons on the imine substrate. (C) 1997 Elsevier Science Ltd.

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页码：7487 / 7490

页数：4

相关论文

共 31 条

[1] RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS [J].

BAKOS, J ;

OROSZ, A ;

HEIL, B ;

LAGHMARI, M ;

LHOSTE, P ;

SINOU, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1684-1685

[2] CATALYTIC AND STRUCTURAL STUDIES OF RHI COMPLEXES OF (-)-(2S,4S)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE - ASYMMETRIC HYDROGENATION OF ACETOPHENONEBENZYLIMINE AND ACETOPHENONE [J].

BAKOS, J ;

TOTH, I ;

HEIL, B ;

SZALONTAI, G ;

PARKANYI, L ;

FULOP, V .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :263-276

[3] CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES [J].

BECALSKI, AG ;

CULLEN, WR ;

FRYZUK, MD ;

JAMES, BR ;

KANG, GJ ;

RETTIG, SJ .

INORGANIC CHEMISTRY, 1991, 30 (26) :5002-5008

[4] Iridium complexes of orthometalated triaryl phosphites: Synthesis, structure, reactivity, and use as imine hydrogenation catalysts [J].

Bedford, RB ;

Castillon, S ;

Chaloner, PA ;

Claver, C ;

Fernandez, E ;

Hitchcock, PB ;

Ruiz, A .

ORGANOMETALLICS, 1996, 15 (19) :3990-3997

[5] HYDRIDE ALKYL AND ALLYL COMPLEXES OF BIS(PI-CYCLOPENTADIENYL)TITANIUM(3) [J].

BRINTZINGER, HH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :6871-+

[6] Studies on catalytic asymmetric imine hydrogenation in the presence of reverse micelles: Enhanced enantioselectivity due to surfactant head group coordination [J].

Buriak, JM ;

Osborn, JA .

ORGANOMETALLICS, 1996, 15 (14) :3161-3169

[7] ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].

BURK, MJ ;

FEASTER, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267

[8] CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].

BURK, MJ ;

MARTINEZ, JP ;

FEASTER, JE ;

COSFORD, N .

TETRAHEDRON, 1994, 50 (15) :4399-4428

[9]

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

[10] TITANIUM-CATALYZED REARRANGEMENT AND OLEFIN-EXCHANGE OF GRIGNARD REAGENTS [J].

COOPER, GD ;

FINKBEINER, HL .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1493-&

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