ASYMMETRIC ORGANOLITHIUM ADDITIONS TO IMINES

被引：111

作者：

TOMIOKA, K ^{[1
]}

INOUE, I ^{[1
]}

SHINDO, M ^{[1
]}

KOGA, K ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,ORGAN RES LABS,TODA,SAITAMA 333,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)97146-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of methyllithium with 4-methoxyphenylimine of 1-naphthalenecarbaldehyde (1) in the presence of the chiral ligand A afforded, contrary to 1,4-addition with the cyclohexylimine, the corresponding 1,2-addition product as an optically active amine (2) in 70% ee. © 1990.

引用

页码：6681 / 6684

页数：4

共 34 条

[1] 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

[2] 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

[3] 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

[4] 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

[5] 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

[6] 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

[7] 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

[8] 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

[9] 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

[10] STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN FROM 3(R)-HYDROXYBUTYRIC ACID [J].

IIMORI, T ;

SHIBASAKI, M .

TETRAHEDRON LETTERS, 1985, 26 (12) :1523-1526

← 1 2 3 4 →