Enantioselective Cu-catalyzed conjugate addition of diethylzinc to acyclic aliphatic enones

被引:49
作者
Duncan, AP [1 ]
Leighton, JL [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ol048191o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new P-chiral phosphine bis(sulfonamide) ligand has been developed that allows the Cu-catalyzed enantioselective conjugate addition of Et2Zn to acyclic aliphatic enones. The reactions proceed with excellent levels of enantioselectivity (90-95% ee) with a range of enone substrates, involve the use of only 1.2 equiv of Et2Zn, and give best results at ambient temperature.
引用
收藏
页码:4117 / 4119
页数:3
相关论文
共 21 条
[1]   Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc [J].
Alexakis, A ;
Polet, D ;
Rosset, S ;
March, S .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5660-5667
[2]   Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].
Alexakis, A ;
Benhaim, C ;
Rosse, S ;
Humam, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263
[3]  
Alexakis A, 2001, SYNLETT, P1375
[4]  
Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[5]   Bis(ethylsulfonamide)amines via nucleophilic ring-opening of chiral aziridines. Application to Ti-mediated addition of diethylzinc to benzaldehyde [J].
Cernerud, M ;
Skrinning, A ;
Bergere, I ;
Moberg, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3437-3441
[6]   Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones [J].
Degrado, SJ ;
Mizutani, H ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13362-13363
[7]   Modular peptide-based phosphine ligands-in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones [J].
Degrado, SJ ;
Mizutani, H ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :755-756
[8]   Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353
[9]   New mode of coordination for the dinitrogen ligand:: A dinuclear tantalum complex with a bridging N2 unit that is both side-on and end-on [J].
Fryzuk, MD ;
Johnson, SA ;
Rettig, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :11024-11025
[10]  
Hu XQ, 1999, ANGEW CHEM INT EDIT, V38, P3518, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO