A new and general synthesis of N-substituted fluorinated beta-iminosulfoxides

被引:9
作者
Fustero, S
Navarro, A
Asensio, A
机构
[1] Depto. de Quim. Orgánica, Facultad de Farmacia, 46100 Burjassot, Valencia, Avda. Vicente Andres Estelles s/n
关键词
D O I
10.1016/S0040-4039(97)01051-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of fluorinated imidoyl chlorides 1 with lithium enolates of chiral non-racemic methyl p-tolyl sulfoxide or racemic methyl phenyl sulfoxide 2 gave N-substituted gamma-fluorinated beta-iminosulfoxides 3 in excellent yields as the major tautomer with Z geometry. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4891 / 4894
页数:4
相关论文
共 21 条
[1]   OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].
ANDERSEN, KK ;
FOLEY, JW ;
GAFFIELD, W ;
PAPANIKOLAU, NE ;
PERKINS, RI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+
[2]   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
[3]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[4]   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
[5]   CHIRAL ACETYLENIC SULFOXIDES IN ORGANIC-SYNTHESIS - SECONDARY AMINE CYCLIZATION AND TOTAL SYNTHESIS OF (S)-(-)-CARNEGINE [J].
CHAN, WH ;
LEE, AWM ;
JIANG, LS .
TETRAHEDRON LETTERS, 1995, 36 (05) :715-718
[6]   An efficient and simple entry to N-substituted beta-enamino acid derivatives from 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines [J].
Fustero, S ;
Navarro, A ;
Diaz, D ;
delaTorre, MG ;
Asensio, A ;
Sanz, F ;
Gonzalez, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8849-8859
[7]   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
[8]   A NEW AND CONVENIENT ONE-POT SYNTHESIS OF ALPHA,BETA-UNSATURATED TRIFLUOROMETHYL KETONES [J].
HUANG, WS ;
YUAN, CY .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07) :741-742
[9]   PERFLUOROALKYLATION INITIATED WITH SODIUM DITHIONITE AND RELATED REAGENT SYSTEMS [J].
HUANG, WY .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 58 (01) :1-8
[10]   THE SYNTHESIS AND STRUCTURE OF BETA-ENAMINO SULFOXIDES [J].
KAWECKI, R ;
KOZERSKI, L .
TETRAHEDRON, 1986, 42 (05) :1469-1473