title: Solution- and solid-phase synthesis of 4-hydroxy-4,5-dihydroisoxazole derivatives from enantiomerically pure N-tosyl-2,3-aziridine alcohols.
abstract: [reaction: see text] 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 using hydroxy Merrifield-supported nitroacetic acid ester.
authors.affiliation: Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale del Risorgimento, 4, I-40136 Bologna, Italy. righi@ms.fci.unibo.it
authors.forename: Paolo
authors.initials: P
authors.lastname: Righi
authors.forename: Noemi
authors.initials: N
authors.lastname: Scardovi
authors.forename: Emanuela
authors.initials: E
authors.lastname: Marotta
authors.forename: Peter
authors.initials: P
authors.lastname: ten Holte
authors.forename: Binne
authors.initials: B
authors.lastname: Zwanenburg