2-AMINO-1-PHENYL-1,3-PROPANEDIOL DERIVATIVES - NEW LIGANDS FOR ASYMMETRIC 1,4-ADDITION OF ORGANOZINC REAGENTS TO ENONES

被引:20
作者
FUJISAWA, T
ITOH, S
SHIMIZU, M
机构
关键词
D O I
10.1246/cl.1994.1777
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of (1S,2S)-3-benzyloxy-2-morpholino-1-phenylpropanol derived readily from (1S,2S)-2-amino-1-phenyl-1,3-propanediol and nickel acetylacetonate, diethylzinc added to alpha,beta-unsaturated ketones to give alkylated product in high optical purity (up to 95%ee). The effects of solvents and additives and the use of such ligands as a chiral catalyst were also investigated.
引用
收藏
页码:1777 / 1780
页数:4
相关论文
共 26 条
[1]   ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES USING NICL2-CHIRAL BETA-DIAMINE COMPLEX AS CATALYST [J].
ASAMI, M ;
USUI, K ;
HIGUCHI, S ;
INOUE, S .
CHEMISTRY LETTERS, 1994, (02) :297-298
[2]   ASYMMETRIC AMPLIFICATION IN NICKEL-CATALYZED CONJUGATE ADDITION TO CHALCONE [J].
BOLM, C .
TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :701-704
[3]  
BOLM C, 1992, SYNLETT, P439
[4]   CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINC COMPOUNDS TO CHALCONES [J].
BOLM, C ;
EWALD, M ;
FELDER, M .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1205-1215
[5]   OPTICALLY-ACTIVE BIPYRIDINES IN NICKEL CATALYZED ENANTIOSELECTIVE CONJUGATE ADDITION TO ENONES [J].
BOLM, C ;
EWALD, M .
TETRAHEDRON LETTERS, 1990, 31 (35) :5011-5012
[6]   CHLORAMPHENICOL (CHLOROMYCETIN) .5. SYNTHESIS [J].
CONTROULIS, J ;
REBSTOCK, MC ;
CROOKS, HM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (07) :2463-2468
[7]   ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES [J].
COREY, EJ ;
NAEF, R ;
HANNON, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7114-7116
[8]   CONJUGATE ADDITION OF DIETHYLZINC TO ENONES CATALYZED BY HOMOGENEOUS AND SUPPORTED CHIRAL NI-COMPLEXES - COOPERATIVE EFFECT OF THE SUPPORT ON ENANTIOSELECTIVITY [J].
CORMA, A ;
IGLESIAS, M ;
MARTIN, MV ;
RUBIO, J ;
SANCHEZ, F .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :845-848
[9]   CHLOROMYCETIN, A NEW ANTIBIOTIC FROM A SOIL ACTINOMYCETE [J].
EHRLICH, J ;
BARTZ, QR ;
SMITH, RM ;
JOSLYN, DA ;
BURKHOLDER, PR .
SCIENCE, 1947, 106 (2757) :417-417
[10]   ENANTIOFACE-DIFFERENTIATING 1,4-ADDITION OF METHYL GRIGNARD-REAGENT TO 1,3-DIPHENYL-2-PROPEN-1-ONE [J].
IMAMOTO, T ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1980, (01) :45-46