New chiral ligands derived from (S)-leucine for the enantioselective addition of diethylzinc to aldehydes

被引:29
作者
Kawanami, Y [1 ]
Mitsuie, T
Miki, M
Sakamoto, T
Nishitani, K
机构
[1] Kagawa Univ, Dept Biochem & Food Sci, Miki, Kagawa 7610795, Japan
[2] Kagawa Univ, Dept Chem, Fac Educ, Takamatsu, Kagawa 7608522, Japan
关键词
chiral ligands; enantioselective addition; (S)-leucine;
D O I
10.1016/S0040-4020(99)00971-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series of chiral beta-amino alcohols derived from (S)-leucine has been synthesized. The amino alcohol possessing a piperidine ring and a phenethyl group on the carbinol carbon atom was found to be an efficient ligand to catalyze the enantioselective addition of diethylzinc to aromatic (up to 97% ee) and aliphatic (up to 95% ee) aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:175 / 178
页数:4
相关论文
共 21 条
[1]   Novel ligands derived from S-tyrosine for the enantioselective addition of diethylzinc to aldehydes [J].
Beliczey, J ;
Giffels, G ;
Kragl, U ;
Wandrey, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1529-1530
[2]   Chiral relay auxiliaries [J].
Bull, SD ;
Davies, SG ;
Fox, DJ ;
Garner, AC ;
Sellers, TGR .
PURE AND APPLIED CHEMISTRY, 1998, 70 (08) :1501-1506
[3]   NEW BETA-AMINO ALCOHOLS DERIVED FROM L-VALINE AS CHIRAL INDUCTORS FOR ENANTIOSELECTIVE REDUCTIONS OF, AND NUCLEOPHILIC ADDITIONS TO CARBONYL-COMPOUNDS [J].
DELAIR, P ;
EINHORN, C ;
EINHORN, J ;
LUCHE, JL .
TETRAHEDRON, 1995, 51 (01) :165-172
[4]  
GWLEY RE, 1996, PRINCIPLES ASYMMETRI
[5]   Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs [J].
Kitamura, M ;
Suga, S ;
Oka, H ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9800-9809
[6]   Asymmetric addition of dialkylzincs to benzaldehyde derivatives catalyzed by chiral β-amino alcohols.: Evidence for the monomeric alkylzinc aminoalkoxide as catalyst [J].
Kitamura, M ;
Oka, H ;
Noyori, R .
TETRAHEDRON, 1999, 55 (12) :3605-3614
[7]   Homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol - Origin of the distinct differences in solution-phase behavior and crystal structures [J].
Kitamura, M ;
Yamakawa, M ;
Oka, H ;
Suga, S ;
Noyori, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (09) :1173-1181
[8]   ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].
KITAMURA, M ;
OKADA, S ;
SUGA, S ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036
[9]   CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].
KITAMURA, M ;
SUGA, S ;
KAWAI, K ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072
[10]   ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].
NOYORI, R ;
KITAMURA, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69