Enantioselective addition of diethylzinc to benzaldehyde in the presence of sulfur-containing pyridine ligands

被引:31
作者
Chelucci, G
Berta, D
Fabbri, D
Pinna, GA
Saba, A
Ulgheri, F
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[2] CNR, Ist Applicaz Tecn Chim Avanzate Problemi Agro, I-07100 Sassari, Italy
[3] CNR, Dipartimento Farmaco Tossicol, I-07100 Sassari, Italy
关键词
D O I
10.1016/S0957-4166(98)00167-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diastereomerically pure hydroxy and thiol derivatives of (5S,7S)-5,7-methane-6,6-dimethyl-2-phenyl-5,6,7,8- tetrahydroquinoline were prepared and assessed in the enantioselective addition of diethylzinc to benzaldehyde: enantioselectivities up to 62% were obtained. (C) 1998 Elsevier Science Ltd. AII rights reserved.
引用
收藏
页码:1933 / 1940
页数:8
相关论文
共 38 条
[1]  
ANGELL RM, 1997, J CHEM SOC CHEM COMM, P919
[2]  
BELLEY M, 1989, J ORG CHEM, V54, P713
[3]   Enantioselective palladium catalyzed allylic substitution with new chiral pyridine-phosphine ligands [J].
Brunel, JM ;
Constantieux, T ;
Labande, A ;
Lubatti, F ;
Buono, G .
TETRAHEDRON LETTERS, 1997, 38 (34) :5971-5974
[4]   Enantioselective catalysis.: Part 119:: New chiral 2-(2-pyridinyl)oxazoline ligands containing an additional optically active substituent in the pyridine system [J].
Brunner, H ;
Störiko, R ;
Nuber, B .
TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :407-422
[5]   Enantioselective palladium catalyzed allylic substitution with sulfur-containing pyridine ligands [J].
Chelucci, G ;
Cabras, MA .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :965-966
[6]   Chiral 8-amino substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethylmethanoquinolines as chiral ligands for enantioselective catalysis: Palladium catalysed allylic substitution and addition of diethylzinc to benzaldehyde [J].
Chelucci, G ;
Pinna, GA ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2571-2578
[7]   Chiral sulfoxides and sulfides tethered to pyridines as ligands for enantioselective catalysis: Palladium catalyzed allylic substitution and addition of diethylzinc to benzaldehyde [J].
Chelucci, G ;
Berta, D ;
Saba, A .
TETRAHEDRON, 1997, 53 (10) :3843-3848
[8]   New chiral C-2-symmetric bis(oxazolinylpyridinyl)dioxolane ligands for asymmetric catalysis: palladium catalysed allylic substitution [J].
Chelucci, G .
TETRAHEDRON-ASYMMETRY, 1997, 8 (16) :2667-2670
[9]   Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution [J].
Chelucci, G ;
Medici, S ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3183-3184
[10]   Enantioselective palladium catalyzed allylic substitution with 2,2′-bipyridine ligands [J].
Chelucci, G ;
Pinna, GA ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1998, 9 (04) :531-534