Highly enantioselective 1,4-addition of diorganozinc reagents to cyclic enones using chiral diphosphite ligands derived from H8-binaphthol

被引:55
作者
Liang, L
Au-Yeung, TTL
Chan, ASC [1 ]
机构
[1] Hong Kong Polytech Univ, Inst Mol Technol Drug Discovery, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
[3] Guangdong Univ Technol, Fac Chem Engn & Light Ind, Guangzhou, Peoples R China
关键词
D O I
10.1021/o1026581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic High enantioselectivities have been achieved in the 1,4-addition of dialkylzincs to 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone with ee values up to 99% by using chiral aryl diphosphite ligands derived from H-8-binaphthol.
引用
收藏
页码:3799 / 3801
页数:3
相关论文
共 33 条
[11]   Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353
[12]   Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].
Helmchen, G ;
Pfaltz, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345
[13]  
Hu XQ, 1999, ANGEW CHEM INT EDIT, V38, P3518, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO
[14]  
2-P
[15]   1,4-addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system [J].
Kitamura, M ;
Miki, T ;
Nakano, K ;
Noyori, R .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (04) :999-1014
[16]  
Knobel AKH, 1997, SYNLETT, P1429
[17]  
Krause N, 2001, SYNTHESIS-STUTTGART, P171
[18]  
Krause N, 1998, ANGEW CHEM INT EDIT, V37, P283, DOI 10.1002/(SICI)1521-3773(19980216)37:3<283::AID-ANIE283>3.0.CO
[19]  
2-9
[20]   Titanium-catalyzed enantioselective alkynylation of aldehydes [J].
Lu, G ;
Li, XS ;
Chan, WL ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2002, (02) :172-173