SYNTHETICALLY USEFUL C-4 FLUORINATED BUILDING-BLOCKS BEARING A QUATERNARY STEREOCENTER

Authors
ARNONE A BRAVO P FRIGERIO M SALANI G VIANI F
Citation
A. Arnone et al., SYNTHETICALLY USEFUL C-4 FLUORINATED BUILDING-BLOCKS BEARING A QUATERNARY STEREOCENTER, Tetrahedron, 50(47), 1994, pp. 13485-13492
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
47
Year of publication
1994
Pages
13485 - 13492
Database
ISI
SICI code
0040-4020(1994)50:47<13485:SUCFBB>2.0.ZU;2-E
Abstract
the syntheses of 2-fluoromethyl-2-hydroxymehtyl-, 2-(dimethoxy)methyl- 2-fluoromethyl- and 2-carboxy-2-fluoromethyl oxiranes 5, 7, and 8 thro ugh reaction of diazomethane with beta-keto-gamma-fluorosubstituted su lphoxide 1 followed by Pummerer rearrangement are shown. Selected oxir ane opening reactions with nitrogen nucleophiles to give beta, gamma-d ihydroxy-beta-fluoromethyl amine 14 and alpha-hydroxy-alpha-fluorometh yl-beta-amino acid 19 are described.