Synthesis of optically active 2-aminotetraline derivatives via enantioselective ruthenium-catalyzed hydrogenation of ene carbamates

被引:18
作者
Dupau, P [1 ]
Hay, AE [1 ]
Bruneau, C [1 ]
Dixneuf, PH [1 ]
机构
[1] Univ Rennes 1, Inst Chim Rennes, CNRS, UMR 6509, F-35042 Rennes, France
关键词
D O I
10.1016/S0957-4166(01)00153-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enantioselective hydrogenation of prochiral ene carbamates. directly derived from 2-tetralone. was completed using a catalytic ruthenium system generated From Ru(COD)(methallyl)(2). an optically pure diphosphine and a strong acid containing a non-coordinating counter anion. (C) 2001 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码:863 / 867
页数:5
相关论文
共 24 条
[1]   ASYMMETRIC-SYNTHESIS BY METAL BINAP CATALYSTS [J].
AKUTAGAWA, S .
APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :171-207
[2]   Enantioselective catalysis for agrochemicals. The case histories of (S)-metolachlor, (R)-metalaxyl and clozylacon [J].
Blaser, HU ;
Spindler, F .
TOPICS IN CATALYSIS, 1997, 4 (3-4) :275-282
[3]   A three-step procedure for asymmetric catalytic reductive amidation of ketones [J].
Burk, MJ ;
Casy, G ;
Johnson, NB .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6084-6085
[4]   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
[5]   Asymmetric synthesis of β-amino alcohols and 1,2-diamines through DuPHOS-Rh catalysed hydrogenation [J].
Burk, MJ ;
Johnson, NB ;
Lee, JR .
TETRAHEDRON LETTERS, 1999, 40 (36) :6685-6688
[6]   A new route to ene carbamates, precursors to benzoindolizinones through sequential asymmetric hydrogenation and cyclization [J].
Couture, A ;
Deniau, E ;
Lebrun, S ;
Grandclaudon, P ;
Carpentier, JF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (08) :1403-1407
[7]   P-C bond splitting reactions in ruthenium(II) complexes of Binap and MeO-Biphep using CF3SO3H and HBF4.: A novel Ru-F-H interaction [J].
den Reijer, CJ ;
Wörle, M ;
Pregosin, PS .
ORGANOMETALLICS, 2000, 19 (03) :309-316
[8]   Alternative synthesis of the chiral atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation [J].
Devocelle, M ;
Mortreux, A ;
Agbossou, F ;
Dormoy, JR .
TETRAHEDRON LETTERS, 1999, 40 (24) :4551-4554
[9]  
Dobbs DA, 2000, ANGEW CHEM INT EDIT, V39, P1992, DOI 10.1002/1521-3773(20000602)39:11<1992::AID-ANIE1992>3.0.CO
[10]  
2-W