Catalytic use of chiral phosphine ligands in asymmetric Pauson-Khand reactions

被引:82
作者
Hiroi, K [1 ]
Watanabe, T [1 ]
Kawagishi, R [1 ]
Abe, I [1 ]
机构
[1] Tohoku Pharmaceut Univ, Dept Synthet Organ Chem, Aoba Ku, Sendai, Miyagi 9818558, Japan
关键词
D O I
10.1016/S0957-4166(99)00570-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Catalytic asymmetric Pauson-Khand reactions with chiral bidentate phosphines as ligands have been successfully accomplished. The catalytic use of (S)-BINAP as a ligand was demonstrated to be the most effective in the cobalt-catalyzed reactions of 1,6-enynes, providing a facile entry to optically active 2-cyclopentenone derivatives with high enantioselectivity. A plausible mechanism for the asymmetric induction is proposed on the basis of the stereochemical outcome obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:797 / 808
页数:12
相关论文
共 33 条
[1]   The tert-butylsulfinyl group as a highly efficient chiral auxiliary in asymmetric Pauson-Khand reactions [J].
Adrio, J ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7411-7412
[2]   PRACTICAL ASYMMETRIC VERSION OF THE INTERMOLECULAR PAUSON-KHAND REACTION [J].
BERNARDES, V ;
VERDAGUER, X ;
KARDOS, N ;
RIERA, A ;
MOYANO, A ;
PERICAS, MA ;
GREENE, AE .
TETRAHEDRON LETTERS, 1994, 35 (04) :575-578
[3]   OPTICALLY-ACTIVE TRANSITION-METAL COMPLEXES .95. OPTICALLY PURE 3A,4,5,6,7,7A-HEXAHYDRO-2-PHENYL-4,7-METHANO-1H-INDEN-1-ONE VIA THE ASYMMETRIC KHAND REACTION [J].
BLADON, P ;
PAUSON, PL ;
BRUNNER, H ;
EDER, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 355 (1-3) :449-454
[4]   CHIRAL BUILDING-BLOCKS FOR FUSED CYCLOPENTANOIDS - ENANTIOSELECTIVE SYNTHESIS OF 5-METHYLBICYCLO[3.3.0]OCT-1-ENE-3,6-DIONE AND DERIVATIVES [J].
BROOKS, DW ;
WOODS, KW .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :2036-2039
[5]   The first alkyne-dicobaltcarbonyl complex with a bidentate chiral ligand with Co-P and Co-N coordination [J].
Castro, J ;
Moyano, A ;
Pericàs, MA ;
Riera, A ;
Alvarez-Larena, A ;
Piniella, JF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 585 (01) :53-58
[6]   ASYMMETRIC-SYNTHESIS OF BICYCLO[4.3.0]NONAN-8-ONES BY INTRAMOLECULAR PAUSON-KHAND REACTION [J].
CASTRO, J ;
MOYANO, A ;
PERICAS, MA ;
RIERA, A ;
GREENE, AE .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :307-310
[7]   DIASTEREOSELECTIVITY IN THE INTERMOLECULAR PAUSON-KHAND REACTION OF CHIRAL 2-ALKYNOATES [J].
FONQUERNA, S ;
MOYANO, A ;
PERICAS, MA ;
RIERA, A .
TETRAHEDRON, 1995, 51 (14) :4239-4254
[8]   Totally stereocontrolled intermolecular Pauson-Khand reactions of N-(2-alkynoyl) sultams [J].
Fonquerna, S ;
Moyano, A ;
Pericas, MA ;
Riera, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10225-10226
[9]  
Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
[10]  
2-O