Chiral Lewis acid-catalyzed enantioselective Michael reactions in water

被引:23
作者
Kobayashi, S [1 ]
Kakumoto, K
Mori, Y
Manabe, K
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Tokyo, Japan
[2] JST, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1092/6GRQ-YRVV-6KU3-RHGX
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric Michael reactions of beta-ketoesters with enones were effectively catalyzed by complexes of silver salts and BINAP derivatives in water. The reactions have proved to give Michael adducts in high yields with high enantioselectivities. These reactions are the first example of Lewis acid-catalyzed asymmetric Michael reactions in water.
引用
收藏
页码:247 / 249
页数:3
相关论文
共 24 条
[1]   Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes [J].
Bernardi, A ;
Karamfilova, K ;
Sanguinetti, S ;
Scolastico, C .
TETRAHEDRON, 1997, 53 (38) :13009-13026
[2]   ASYMMETRIC CATALYSIS .18. ENANTIOSELECTIVE MICHAEL ADDITIONS WITH OPTICALLY-ACTIVE COII/DIAMINE CATALYSTS [J].
BRUNNER, H ;
HAMMER, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (04) :312-313
[3]  
Christoffers J, 2000, EUR J ORG CHEM, V2000, P701, DOI 10.1002/(SICI)1099-0690(200003)2000:5<701::AID-EJOC701>3.0.CO
[4]  
2-5
[5]   C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates [J].
Evans, DA ;
Rovis, T ;
Kozlowski, MC ;
Tedrow, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1994-1995
[6]  
Fringuelli F., 1998, ORGANIC SYNTHESIS WA, P250
[7]   Asymmetric Mukaiyama-Michael addition of acyclic enones catalyzed by allo-threonine-derived B-aryloxazaborolidinones [J].
Harada, T ;
Iwai, H ;
Takatsuki, H ;
Fujita, K ;
Kubo, M ;
Oku, A .
ORGANIC LETTERS, 2001, 3 (13) :2101-2103
[8]   Catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes [J].
Ji, JG ;
Barnes, DM ;
Zhang, J ;
King, SA ;
Wittenberger, SJ ;
Morton, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10215-10216
[9]   Ytterbium triflate catalyzed Michael additions of beta-ketoesters in water [J].
Keller, E ;
Feringa, BL .
TETRAHEDRON LETTERS, 1996, 37 (11) :1879-1882
[10]   A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates [J].
Kitajima, H ;
Ito, K ;
Katsuki, T .
TETRAHEDRON, 1997, 53 (50) :17015-17028