ENANTIOSELECTIVE REACTION OF AN IMINE WITH METHYLLITHIUM CATALYZED BY A CHIRAL LIGAND

被引:66
作者
INOUE, I
SHINDO, M
KOGA, K
KANAI, M
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
10.1016/0957-4166(95)00331-I
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantioselective reaction of benzaldehyde 4-anisidineimine 1 with methyllithium in toluene was mediated by a series of chiral aminoethers 3-11 to give the corresponding amine 2 in good to moderate ee. The chiral tridentate aminoethers 7-11 are superior to the bidentate ligands 3-6, Lithium bromide affects significantly the enantioselectivity in the catalytic reaction, but not in the stoichiometric reaction.
引用
收藏
页码:2527 / 2533
页数:7
相关论文
共 21 条
[1]  
Bosnich B., 1986, ASYMMETRIC CATALYSIS
[2]  
BUNN BJ, 1993, J ORG CHEM, V58, P532
[3]   PREPARATION AND ACTIVITY OF BETA-SUBSTITUTED ACETYLCHOLINE IODIDES [J].
COCOLAS, GH ;
ROBINSON, EC ;
DEWEY, WL ;
SPAULDING, TC .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1971, 60 (11) :1749-+
[4]  
DENMARK SE, 1994, J AM CHEM SOC, V116, P8979
[5]   ASYMMETRIC 1,2-ADDITION OF ORGANOLITHIUMS TO ALDIMINES CATALYZED BY CHIRAL LIGAND [J].
INOUE, I ;
SHINDO, M ;
KOGA, K ;
TOMIOKA, K .
TETRAHEDRON, 1994, 50 (15) :4429-4438
[6]   ENANTIOSELECTIVE ALKYLATION OF N-(TRIMETHYLSILYL)BENZALDEHYDE IMINE [J].
ITSUNO, S ;
YANAKA, H ;
HACHISUKA, C ;
ITO, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1341-1342
[7]   CATALYTIC ASYMMETRIC CONJUGATE ADDITION OF GRIGNARD-REAGENTS MEDIATED BY COPPER(I)-CHIRAL BIDENTATE PHOSPHINE COMPLEX [J].
KANAI, M ;
TOMIOKA, K .
TETRAHEDRON LETTERS, 1995, 36 (24) :4275-4278
[8]   ENANTIOSELECTIVE ETHYLATION OF N-(AMIDOBENZYL)BENZOTRIAZOLES CATALYZED BY CHIRAL AMINOALCOHOLS [J].
KATRITZKY, AR ;
HARRIS, PA .
TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :437-442
[9]   ENANTIOSELECTIVE 1,2-ADDITION OF GRIGNARD-REAGENTS TO ALDEHYDES USING CHIRAL DIAMINES [J].
NAKAJIMA, M ;
TOMIOKA, K ;
KOGA, K .
TETRAHEDRON, 1993, 49 (43) :9751-9758
[10]  
Noyori R., 1994, ASYMMETRIC CATALYSIS