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
[1]  
Alexakis A, 2000, EUR J ORG CHEM, V2000, P4011, DOI 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO
[2]  
2-D
[3]  
Alexakis A, 1999, SYNLETT, P1811
[4]   Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].
Alexakis, A ;
Vastra, J ;
Burton, J ;
Benhaim, C ;
Mangeney, P .
TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872
[5]   Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].
Arnold, LA ;
Imbos, R ;
Mandoli, A ;
de Vries, AHM ;
Naasz, R ;
Feringa, BL .
TETRAHEDRON, 2000, 56 (18) :2865-2878
[6]   CHIRAL ECONOMIC SYNTHESIS OF (R)-MUSCONE AND (S)-MUSCONE USING CYCLOFRAGMENTATION OF EPOXYSULFONES [J].
BRANCA, Q ;
FISCHLI, A .
HELVETICA CHIMICA ACTA, 1977, 60 (03) :925-944
[7]  
Chataigner I, 2001, CHEM-EUR J, V7, P2628, DOI 10.1002/1521-3765(20010618)7:12<2628::AID-CHEM26280>3.0.CO
[8]  
2-7
[9]  
Chataigner I, 2000, ANGEW CHEM INT EDIT, V39, P916, DOI 10.1002/(SICI)1521-3773(20000303)39:5<916::AID-ANIE916>3.0.CO
[10]  
2-M