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

Stefano Cicchi; Massimo Corsi; Alberto Brandi; Andrea Goti

doi:10.1021/jo0157573

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

J Org Chem. 2002 Mar 8;67(5):1678-81. doi: 10.1021/jo0157573.

Authors

Stefano Cicchi¹, Massimo Corsi, Alberto Brandi, Andrea Goti

Affiliation

¹ 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.

PMID: 11871902
DOI: 10.1021/jo0157573

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.