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
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.
引用
收藏
页码:7487 / 7490
页数:4
相关论文
共 31 条
[22]   CP2TICL2-CATALYZED GRIGNARD EXCHANGE-REACTIONS WITH ACETYLENES - A CONVENIENT METHOD FOR PREPARATION OF E-ALKENYL GRIGNARD-REAGENTS [J].
SATO, F ;
ISHIKAWA, H ;
SATO, M .
TETRAHEDRON LETTERS, 1981, 22 (01) :85-88
[23]   CP2TICL2-CATALYZED GRIGNARD REACTIONS .2. REACTIONS WITH KETONES AND ALDEHYDES [J].
SATO, F ;
JINBO, T ;
SATO, M .
TETRAHEDRON LETTERS, 1980, 21 (22) :2171-2174
[24]   NOVEL DIPHOSPHINOIRIDIUM CATALYSTS FOR THE ENANTIOSELECTIVE HYDROGENATION OF N-ARYLKETIMINES [J].
SPINDLER, F ;
PUGIN, B ;
BLASER, HU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :558-559
[25]   IRIDIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF PROCHIRAL IMINES - PROTIC AMINES AS CATALYST IMPROVERS [J].
TANI, K ;
ONOUCHI, J ;
YAMAGATA, T ;
KATAOKA, Y .
CHEMISTRY LETTERS, 1995, (10) :955-956
[26]   DIMERIC TITANOCENE HYDRIDE-HYDRIDOMAGNESIUM CHLORIDE AND BROMIDE COMPLEXES - CRYSTAL-STRUCTURES OF THE TETRAMETHYLCYCLOPENTADIENYL DERIVATIVES [J].
TROYANOV, SI ;
VARGA, V ;
MACH, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 461 (1-2) :85-90
[27]   Highly enantioselective imine hydrosilylation using (S,S)-ethylenebis(eta(5)-tetrahydroindenyl)titanium difluoride [J].
Verdaguer, X ;
Lange, UEW ;
Reding, MT ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6784-6785
[28]   ASYMMETRIC TITANOCENE-CATALYZED HYDROGENATION OF IMINES [J].
WILLOUGHBY, CA ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7562-7564
[29]   CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES WITH A CHIRAL TITANOCENE CATALYST - SCOPE AND LIMITATIONS [J].
WILLOUGHBY, CA ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :8952-8965
[30]   CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES WITH A CHIRAL TITANOCENE CATALYST - KINETIC AND MECHANISTIC INVESTIGATIONS [J].
WILLOUGHBY, CA ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :11703-11714