NUCLEOPHILIC RING-OPENING OF 3-F-ALKYL 2,3-EPOXYPROPANOATES - ACCESS TO ALPHA,BETA-DIFUNCTIONAL BETA-F-ALKYLPROPANOATES

Authors
LANIER M LEBLANC M PASTOR R
Citation
M. Lanier et al., NUCLEOPHILIC RING-OPENING OF 3-F-ALKYL 2,3-EPOXYPROPANOATES - ACCESS TO ALPHA,BETA-DIFUNCTIONAL BETA-F-ALKYLPROPANOATES, Tetrahedron, 52(46), 1996, pp. 14631-14640
Citations number
52
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
46
Year of publication
1996
Pages
14631 - 14640
Database
ISI
SICI code
0040-4020(1996)52:46<14631:NRO32->2.0.ZU;2-U
Abstract
Nucleophilic ring opening of 3-F-alkyl 2,3-epoxypropanoates 1 with pri mary amines or chloride ions leads regioselectively to 2-substituted 3 -F-alkyl 3-hydroxypropanoates. Azidolysis is not so selective but 2-az ido 3-F-alkyl 3-hydroxypropanoates 7 are still the major products. Wit h NaBH4 in alcoholic media (EtOH, OcOH) 2-alkoxy 3-F-alkyl 1,3-propane diols (2=Et, 3=Oc) are obtained. Copyright (C) 1996 Elsevier Science L td