Stereoselective Synthesis of Fluorinated Isoxazolidines and 2, 3??Dihydroisoxazoles: A Cycloadditive Route to Enantiomerically Pure Amino Fluoro Alcohols

…, P Bravo, W Panzeri, C Pesenti, F Viani

Index: Bruche, Luca; Arnone, Alberto; Bravo, Pierfrancesco; Panzeri, Walter; Pesenti, Cristina; Viani, Fiorenza European Journal of Organic Chemistry, 1999 , # 7 p. 1665 - 1670

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Citation Number: 8

Abstract

Abstract 3-(Fluoroalkyl) isoxazolidines 6 and-2, 3-dihydroisoxazoles 8 have been obtained in enantiomerically pure form with good diastereoselectivity by 1, 3-dipolar cycloaddition of diethyl fumarate and dimethylacetylene dicarboxylate, respectively, to the chiral fluorinated nitrone (R)-5. The latter has been prepared from the β-fluoromethyl-β-oxo sulfoxide (RS)-1, by a synthetic sequence where the chiral and enantiomerically pure sulfinyl function acts ...