SYNTHESIS OF ALPHA-FLUORO-BETA-HYDROXY ALKYLSULFANYL ESTERS VIA A NUCLEOPHILIC FLUORINATION OF SULFIDES

Authors
JOUEN C LEMAITRE S LEQUEUX T POMMELET JC
Citation
C. Jouen et al., SYNTHESIS OF ALPHA-FLUORO-BETA-HYDROXY ALKYLSULFANYL ESTERS VIA A NUCLEOPHILIC FLUORINATION OF SULFIDES, Tetrahedron, 54(36), 1998, pp. 10801-10810
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
36
Year of publication
1998
Pages
10801 - 10810
Database
ISI
SICI code
0040-4020(1998)54:36<10801:SOAAEV>2.0.ZU;2-7
Abstract
By halogen-exchange reaction using NEt3-3HF as fluoride source, methyl 2-fluoro-2-alkylsulfanyl acetate 3a-d could be obtained in good yield s. Their ester enolates reacted with aromatic or aliphatic aldehydes, to lead to methyl alpha-alkylsulfanyl-alpha-fluoro-beta-hydroxy esters 4-8. By using benzaldehyde as electrophile, the retro-aldol reaction could be favorised by a temperature effect. The selective formation of the syn or the anti diastereoisomers has been controled. (C) 1998 Els evier Science Ltd. All rights reserved.