ASYMMETRIC 1,2-ADDITION OF ORGANOLITHIUMS TO ALDIMINES CATALYZED BY CHIRAL LIGAND

被引:79
作者
INOUE, I
SHINDO, M
KOGA, K
TOMIOKA, K
机构
[1] OSAKA UNIV,INST SCI & IND RES,IBARAKI,OSAKA 567,JAPAN
[2] TANABE SEIYAKU CO LTD,ORGAN CHEM RES LAB,TODA,SAITAMA 335,JAPAN
[3] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/S0040-4020(01)89376-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric 1,2-addition reaction of organolithiums with imines 3, 7 was catalyzed by a 0.05-1.3 equivalent of a chiral amino ether 2 to provide the corresponding optically active amines 4, 8.
引用
收藏
页码:4429 / 4438
页数:10
相关论文
共 35 条
[1]  
Bosnich B., 1986, ASYMMETRIC CATALYSIS
[2]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].
CAINELLI, G ;
PANUNZIO, M ;
GIACOMINI, D ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880
[3]   ENANTIOSELECTIVE SYNTHESIS OF PRIMARY AMINES VIA GRIGNARD ADDITIONS TO STEREOGENIC N-(ALPHA-PHENYL-BETA-(BENZYLOXY)ETHYL)NITRONES [J].
CHANG, ZY ;
COATES, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3475-3483
[4]   A FACILE ENTRY TO 3-(1-HYDROXYETHYL)-2-AZETIDINONES FROM METHYL(R)-3-HYDROXYBUTANOATE BASED ON THE ESTER ENOLATE-ALDIMINE CONDENSATION [J].
CHIBA, T ;
NAGATSUMA, M ;
NAKAI, T .
CHEMISTRY LETTERS, 1984, (11) :1927-1930
[5]   ORGANOLITHIUM ADDITION TO ALDEHYDE DIMETHYLHYDRAZONES - A HIGHLY DIASTEREOCONTROLLED SYNTHESIS OF THREO 2-AMINO ALCOHOLS AND (1R,2R)-(-)-NORPSEUDOEPHEDRINE [J].
CLAREMON, DA ;
LUMMA, PK ;
PHILLIPS, BT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8265-8266
[6]   SYNTHESIS OF SECONDARY AND TERTIARY CARBINAMINES FROM N-ALKYLIDENEARENESULFENAMIDES AND ALKYLLITHIUM AND ARYLLITHIUM REAGENTS [J].
DAVIS, FA ;
MANCINELLI, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) :398-399
[7]   ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED PRIMARY AMINES BY NUCLEOPHILIC-ADDITION TO ALDEHYDE-SAMP HYDRAZONES [J].
ENDERS, D ;
SCHUBERT, H ;
NUBLING, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (12) :1109-1110
[8]   A STEREOSELECTIVE SYNTHESIS OF N-BOC-ALPHA-AMINO ALCOHOLS AND ALPHA-AMINO-ACIDS [J].
ERMERT, P ;
MEYER, J ;
STUCKI, C ;
SCHNEEBELI, J ;
OBRECHT, JP .
TETRAHEDRON LETTERS, 1988, 29 (11) :1265-1268
[9]   STEREOSPECIFIC SYNTHESIS OF N-BENZOYL-L-DAUNOSAMINE AND L-RISTOSAMINE [J].
FUGANTI, C ;
GRASSELLI, P ;
PEDROCCHIFANTONI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :909-910
[10]   PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].
HART, DJ ;
KANAI, K ;
THOMAS, DG ;
YANG, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294