Highly enantioselective Reformatsky reaction of ketones: Chelation-assisted enantioface discrimination

被引:36
作者
Ojida, A
Yamano, T
Taya, N
Tasaka, A
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Higashi Ku, Fukuoka 8128581, Japan
[2] Takeda Chem Ind Ltd, Med Chem Res Labs, Osaka 5328686, Japan
关键词
D O I
10.1021/ol0263189
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Highly enantioselective Reformatsky reaction of ketones was accomplished using cinchona alkaloids as chiral ligands. Chelation with the sp(2)-nitrogen adjacent to the reactive carbonyl center contributed the enantioface discrimination for the high enantioselectivities.
引用
收藏
页码:3051 / 3054
页数:4
相关论文
共 22 条
[11]   ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES [J].
LOWENTHAL, RE ;
ABIKO, A ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1990, 31 (42) :6005-6008
[12]   Chiral discrimination promoted by (1S,2S)-1-phenyl-2-amino-1,3-propanediol derivatives in the asymmetric reformatsky reaction [J].
Mastantuono, A ;
Pini, D ;
Rolfini, C ;
Salvadori, P .
CHIRALITY, 1995, 7 (07) :499-504
[13]  
MI AQ, 1995, TETRAHEDRON-ASYMMETR, V6, P2641
[14]   Asymmetric syntheses .26. Catalytic enantioselective syntheses of beta-hydroxy esters via double chiral induction in asymmetric Reformatsky reactions [J].
Mi, AQ ;
Wang, ZY ;
Zhang, JM ;
Jiang, YZ .
SYNTHETIC COMMUNICATIONS, 1997, 27 (09) :1469-1473
[15]   Enantioselective reactions of radicals at the α position of γ-lactams [J].
Porter, NA ;
Feng, H ;
Kavrakova, IK .
TETRAHEDRON LETTERS, 1999, 40 (37) :6713-6716
[16]   Catalytic asymmetric organozinc additions to carbonyl compounds [J].
Pu, L ;
Yu, HB .
CHEMICAL REVIEWS, 2001, 101 (03) :757-824
[17]   First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives [J].
Ramón, DJ ;
Yus, M .
TETRAHEDRON, 1998, 54 (21) :5651-5666
[18]   Enantioselective intermolecular free radical conjugate additions. Application of a pyrazole template [J].
Sibi, MP ;
Shay, JJ ;
Ji, JG .
TETRAHEDRON LETTERS, 1997, 38 (34) :5955-5958
[19]   STEREOSELECTIVE ADDITION-REACTION OF DIETHYLZINC TO ALDEHYDES, CATALYZED BY CINCHONA ALKALOIDS [J].
SMAARDIJK, AA ;
WYNBERG, H .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :135-137
[20]   ENANTIOSELECTIVE REFORMATSKY REACTION WITH KETONES - ASYMMETRIC-SYNTHESIS OF BETA-(TERT-HYDROXY)ESTERS [J].
SOAI, K ;
OSHIO, A ;
SAITO, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :811-812