title: Straightforward synthesis of enantiomerically pure (3S,4R)- and (3R,4S)-3,4-isopropylidenedioxypyrroline 1-oxide, precursors of functionalized cis-dihydroxy azaheterocycles, by a novel "one-pot" procedure.
abstract: The enantiomerically pure nitrone 3, a valuable precursor of mono- and bicyclic azaheterocycles, has been synthesized in 57% yield by a novel "one-pot" process starting from lactol 1, in turn readily available from D-arabinose. The same process, consisting of reaction with a O-silyl-protected hydroxylamine followed by mesylation in pyridine, furnished ent-3 in 55% yield when applied to L-arabinose.
authors.affiliation: Dipartimento di Chimica Organica Ugo Schiff, Centro di Studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Università degli Studi di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino, Firenze, Italy.
authors.forename: Stefano
authors.initials: S
authors.lastname: Cicchi
authors.forename: Massimo
authors.initials: M
authors.lastname: Corsi
authors.forename: Alberto
authors.initials: A
authors.lastname: Brandi
authors.forename: Andrea
authors.initials: A
authors.lastname: Goti