Synthesis of enantiomerically pure acyclic α-sulfinyl ketimines

被引:9
作者
Ruano, JLG [1 ]
Lorente, A [1 ]
Ramos, JHR [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
关键词
D O I
10.1016/S0957-4166(98)00211-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two different methods to obtain enantiomerically pure N-alkyl and N-aryl alpha-sulfinyl ketimines are reported. Reaction of enantiomerically pure alpha-sulfinyl ketones (1-6) with benzylamine or p-methoxyaniline, in the presence of molecular sieves (3 Angstrom), yields the corresponding of N-benzyl and N-p-methoxyphenyl ketimines (7A-12A and 7B-12B). Better results were achieved by alpha-sulfinylation of ketimines (13A-18A and 13B-18B) with (-)-menthyl p-toluenesulfinate in the presence of lithium (N-arylimines) or magnesium (N-benzylimines) bases. The different tautomeric behaviour of the obtained N-aryl and N-alkyl derivatives is reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2437 / 2450
页数:14
相关论文
共 42 条
[1]   REACTION OF LITHIOENAMINES WITH SULFINATE ESTERS - STEREOSPECIFIC AND STEREOSELECTIVE SYNTHESIS OF BETA-ENAMINO AND BETA-IMINO SULFOXIDES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
RESTELLI, A ;
COZZI, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05) :1183-1186
[2]  
ANNUNZIATA R, 1979, J CHEM SOC P1, P1678
[3]   New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines [J].
Arnone, A ;
Bravo, P ;
Capelli, S ;
Fronza, G ;
Meille, SV ;
Zanda, M ;
Cavicchio, G ;
Crucianelli, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3375-3387
[4]   SYNTHESIS OF NEW OPTICALLY-ACTIVE SULFOXIDES WITH CHELATING PROPERTIES [J].
BALDENIUS, KU ;
KAGAN, HB .
TETRAHEDRON-ASYMMETRY, 1990, 1 (09) :597-610
[5]  
BARROS D, 1992, TETRAHEDRON LETT, V33, P2733
[6]   ALKYLATION OF ENAMINES OF BIS(ETHYLTHIO)ACETALDEHYDE - SYNTHESIS OF NORPYRENOPHORIN [J].
BATES, GS ;
RAMASWAMY, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (19) :904-906
[7]  
CAINE D, 1991, COMPREHENSIVE ORGANI, V3, P32
[8]   APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
CARRENO, MC .
CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760
[9]   STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].
CARRENO, MC ;
RUANO, JLG ;
MARTIN, AM ;
PEDREGAL, C ;
RODRIGUEZ, JH ;
RUBIO, A ;
SANCHEZ, J ;
SOLLADIE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128
[10]   SYNTHESIS AND HYDRIDE REDUCTIONS OF CHIRAL CYCLIC BETA-IMINOSULFOXIDES [J].
CARRENO, MC ;
DOMINGUEZ, E ;
RUANO, JLG ;
PEDREGAL, C ;
RODRIGUEZ, JH .
TETRAHEDRON, 1991, 47 (48) :10035-10044