The brucine N-oxide-promoted asymmetric Pauson-Khand reaction

被引:45
作者
Kerr, WJ [1 ]
Lindsay, DM
Rankin, EM
Scott, JS
Watson, SP
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
amine N-oxides; asymmetric synthesis; cobalt and compounds; cyclopentenones; Pauson-Khand reactions;
D O I
10.1016/S0040-4039(00)00357-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The brucine N-oxide-mediated asymmetric Pauson-Khand reaction has been further investigated. It was found that the best levels of enantioselection were obtained with substituted propargylic alcohol complexes. The studies also revealed that when acetone or 1,2-dimethoxyethane is used as the reaction solvent, enhanced levels of enantioselectivity, up to an enantiomeric ratio of 11:89, are achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3229 / 3233
页数:5
相关论文
共 22 条
[1]   Thermal promotion of the cobalt catalyzed intramolecular Pauson-Khand reaction - An alternative experimental protocol for cyclopentenone synthesis [J].
Belanger, DB ;
O'Mahony, DJR ;
Livinghouse, T .
TETRAHEDRON LETTERS, 1998, 39 (42) :7637-7640
[2]   Hexacarbonyldicobalt-alkyne complexes as convenient Co2(CO)8 surrogates in the catalytic Pauson-Khand reaction [J].
Belanger, DB ;
Livinghouse, T .
TETRAHEDRON LETTERS, 1998, 39 (42) :7641-7644
[3]  
Chung YK, 1999, COORDIN CHEM REV, V188, P297
[4]  
Derdau V, 1998, HETEROCYCLES, V48, P1445
[5]   Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione [J].
Donkervoort, JG ;
Gordon, AR ;
Johnstone, C ;
Kerr, WJ ;
Lange, U .
TETRAHEDRON, 1996, 52 (21) :7391-7420
[6]  
Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
[7]  
2-O
[8]  
GORDON AR, 1995, SYNLETT, P1083
[9]   HIGHLY EFFICIENT ENANTIOSELECTIVE PAUSON-KHAND REACTIONS [J].
HAY, AM ;
KERR, WJ ;
KIRK, GG ;
MIDDLEMISS, D .
ORGANOMETALLICS, 1995, 14 (11) :4986-4988
[10]   The asymmetric Pauson-Khand reaction. A review [J].
Ingate, ST ;
Marco-Contelles, J .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (02) :121-+