Solution- and solid-phase synthesis of 4-hydroxy-4,5-dihydroisoxazole derivatives from enantiomerically pure N-tosyl-2,3-aziridine alcohols.
[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.
Righi
Paolo
P
Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale del Risorgimento, 4, I-40136 Bologna, Italy. righi@ms.fci.unibo.it
Scardovi
Noemi
N
Marotta
Emanuela
E
ten Holte
Peter
P
Zwanenburg
Binne
B