Copper-catalyzed conjugate addition on macrocyclic, cyclic, and acyclic enones with a chiral phosphoramidite ligand having a C2-symmetric amine moiety

被引:63
作者
Choi, YH [1 ]
Choi, JY [1 ]
Yang, HY [1 ]
Kim, YH [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
关键词
D O I
10.1016/S0957-4166(02)00206-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A binaphthol-based phosphoramidite ligand (4.2 mol%) having a C-2-symmetric chiral amine moiety was examined for enantioselective 1,4-additions of dialkylzinc reagents to various macrocyclic, cyclic, and acyclic enones catalyzed by copper triflate-toluene complex (2 mol%) to afford high enantiomeric excess (up to >95% ee). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:801 / 804
页数:4
相关论文
共 39 条
[11]  
CHONG JM, 1995, TETRAHEDRON-ASYMMETR, V6, P409
[12]   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
[13]   Enantioselective conjugate addition of dialkylzinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites [J].
deVries, AHM ;
Meetsma, A ;
Feringa, BL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20) :2374-2376
[14]   Chiral diphosphites derived from D-glucose in the copper-catalyzed conjugate addition of diethylzinc to cyclohexenone [J].
Diéguez, M ;
Ruiz, A ;
Claver, C .
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2895-2900
[15]   Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].
Feringa, BL ;
Pineschi, M ;
Arnold, LA ;
Imbos, R ;
de Vries, AHM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623
[16]   Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353
[17]  
Hu XQ, 1999, ANGEW CHEM INT EDIT, V38, P3518, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO
[18]  
2-P
[19]   Ring closing metathesis guided synthesis of (R)-(-)-muscone [J].
Kamat, VP ;
Hagiwara, H ;
Suzuki, T ;
Ando, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2253-2254
[20]  
Knobel AKH, 1997, SYNLETT, P1429