Cobalt-phosphite-catalyzed asymmetric Pauson-Khand reaction

被引:72
作者
Sturla, SJ [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/jo016038r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A complex formed from dicobalt octacarbonyl and a chiral aryl bisphosphite served as a catalyst for the intramolecular asymmetric Pauson-Ehand reaction. Bicyclic cyclopentenones were obtained in up to 75% enantiomeric excess. For a terminal 1,6-enyne, the incremental enantiomeric excess was found to increase from 4 to 26% over the course of the reaction. The scope of this process was examined for a variety of 1,6- and 1,7-enynes, and a moderate degree of enantioselectivity was maintained only in the case of aryl-substituted 1,6-enynes.
引用
收藏
页码:3398 / 3403
页数:6
相关论文
共 60 条
[1]   CHIRAL ARYL DIPHOSPHITES - A NEW CLASS OF LIGANDS FOR HYDROCYANATION CATALYSIS [J].
BAKER, MJ ;
PRINGLE, PG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1292-1293
[2]   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
[3]   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
[4]  
BILLINGTON DC, 1988, J ORGANOMET CHEM, V354, P243
[5]   CRYSTAL AND MOLECULAR-STRUCTURE OF (ACETYLENE)BIS(TRIMETHYLPHOSPHINE)(TETRACARBONYL)DICOBALT(O) [J].
BONNET, JJ ;
MATHIEU, R .
INORGANIC CHEMISTRY, 1978, 17 (07) :1973-1976
[7]   INFRARED-SPECTRUM OF DICOBALT OCTACARBONYL - RESULTS OF CO-13 ENRICHMENT STUDIES [J].
BOR, G ;
NOACK, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 64 (03) :367-372
[8]   HIGH-TEMPERATURE INFRARED-SPECTRUM OF DICOBALT OCTACARBONYL - PREDOMINANCE OF 3RD ISOMER [J].
BOR, G ;
DIETLER, UK ;
NOACK, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (22) :914-916
[9]  
Brain T, 2001, J AM CHEM SOC, V123, P7184
[10]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283