STEREOSELECTIVE SYNTHESIS OF OPTICALLY PURE GAMMA-FLUORO-BETA-ENAMINOSULFOXIDES AND REDUCTION TO GAMMA-FLUORO-BETA-AMINOSULFOXIDES

被引:22
作者
BRAVO, P [1 ]
CRUCIANELLI, M [1 ]
ZANDA, M [1 ]
机构
[1] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67010 LAQUILA,ITALY
关键词
D O I
10.1016/0040-4039(95)00422-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aza-Wittig reaction of phospha-lambda(5)-azenes with optically pure gamma-fluorosubstituted beta-ketosulfoxides leads to the corresponding beta-enaminosulfoxides, which were easily isolated in diastereomerically pure form. The stereoselective reduction of the enamine 3cb afforded the optically pure beta-sulphinyl-amine 5cb in high overall yield.
引用
收藏
页码:3043 / 3046
页数:4
相关论文
共 21 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]   SYNTHESIS OF NEW OPTICALLY-ACTIVE SULFOXIDES WITH CHELATING PROPERTIES [J].
BALDENIUS, KU ;
KAGAN, HB .
TETRAHEDRON-ASYMMETRY, 1990, 1 (09) :597-610
[3]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[4]  
BRAVO P, 1986, SYNTHESIS-STUTTGART, P579
[5]   DIRECTED RESOLUTION OF ENANTIOMERS VIA LIQUID-CHROMATOGRAPHY OF DIASTEREOMERIC DERIVATIVES .4. EXTREME LIQUID-CHROMATOGRAPHIC SEPARATION EFFECTS IN THE CASE OF DIASTEREOMERIC AMIDES CONTAINING POLAR SUBSTITUENTS [J].
HELMCHEN, G ;
NILL, G ;
FLOCKERZI, D ;
SCHUHLE, W ;
YOUSSEF, MSK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :62-63
[6]   CONJUGATE-ADDITION REACTIONS OF ALPHA-SULFINYL KETIMINE ANIONS WITH A METHYL ALPHA-AMIDOACRYLATE - CONCISE ASYMMETRIC TOTAL SYNTHESES OF (-)-SLAFRAMINE AND (-)-6-EPISLAFRAMINE [J].
HUA, DH ;
PARK, JG ;
KATSUHIRA, T ;
BHARATHI, SN .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2144-2150
[7]  
Johnson A. W., 1993, YLIDES IMINES PHOSPH
[8]   THE SYNTHESIS AND STRUCTURE OF BETA-ENAMINO SULFOXIDES [J].
KAWECKI, R ;
KOZERSKI, L .
TETRAHEDRON, 1986, 42 (05) :1469-1473
[9]   STEREOSELECTIVE PROTONATION AND REDUCTION OF BETA-SULFINYL ENAMINES - X-RAY MOLECULAR-STRUCTURE OF N-BENZYL-2-(PARA-TOLYSULPHINYL)PROPYLAMINE [J].
KAWECKI, R ;
KOZERSKI, L ;
URBANCZYKLIPKOWSKA, Z ;
BOCELLI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2255-2260
[10]  
KLOEK JA, 1978, J ORG CHEM, V43, P1460, DOI 10.1021/jo00401a037