Solution-and Solid-Phase Synthesis of 4-Hydroxy-4, 5-dihydroisoxazole Derivatives from Enantiomerically Pure N-Tosyl-2, 3-aziridine Alcohols

P Righi, N Scardovi, E Marotta, P ten Holte…

Index: Righi, Paolo; Scardovi, Noemi; Marotta, Emanuela; Holte, Peter Ten; Zwanenburg, Binne Organic Letters, 2002 , vol. 4, # 4 p. 497 - 500

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Citation Number: 36

Abstract

Enantiomerically pure N-tosyl-2, 3-aziridine alcohols are directly converted into 4-hydroxy-4, 5-dihydroisoxazole 2-oxides through oxidation to the corresponding aldehydes followed by in situ tandem nitroaldol-intramolecular cyclization. This study was concerned with (i) the selection of a suitable aziridine activation,(ii) the preparation of the target 4-hydroxy-4, 5- dihydroisoxazole derivatives in solution, and (iii) the elaboration of a solid-phase process ...