A NOVEL STEREOSELECTIVE SYNTHESIS OF CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ACID

Authors
TOYOTA A ONO Y KANEKO C HAYAKAWA I
Citation
A. Toyota et al., A NOVEL STEREOSELECTIVE SYNTHESIS OF CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ACID, Tetrahedron letters, 37(47), 1996, pp. 8507-8510
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
47
Year of publication
1996
Pages
8507 - 8510
Database
ISI
SICI code
0040-4039(1996)37:47<8507:ANSSOC>2.0.ZU;2-G
Abstract
A novel method consisting four-step from tert-butyl acrylate (4) and c hloromethyl phenyl sulfoxide (5) for preparing cis-2-fluorocyclopropan e-1-carboxylic acid (cis-3) was elaborated. The method involves initia l formation of the cis-2-phenylsulfinylcyclopropanecarboxylate (cis-6) , fluorination by molecular fluorine to trans-7, reductive desulfonyla tion to the ester (cis-9) and acid-catalyzed hydrolysis to the final p roduct(cis-3). Copyright (C) 1996 Elsevier Science Ltd