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
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