Oxidation of hydroxylamines to nitrones catalyzed by (salen)Mn(III) complexes. Enantioselective synthesis of a protected cis-dihydroxypyrroline N-oxide with Jacobsen catalyst

Authors
Cicchi, S Cardona, F Brandi, A Corsi, M Goti, A
Citation
S. Cicchi et al., Oxidation of hydroxylamines to nitrones catalyzed by (salen)Mn(III) complexes. Enantioselective synthesis of a protected cis-dihydroxypyrroline N-oxide with Jacobsen catalyst, TETRAHEDR L, 40(10), 1999, pp. 1989-1992
Citations number
36
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
10
Year of publication
1999
Pages
1989 - 1992
Database
ISI
SICI code
0040-4039(19990305)40:10<1989:OOHTNC>2.0.ZU;2-V
Abstract
Oxidation of N,N-disubstituted hydroxylamines to nitrones catalyzed by the Jacobsen catalyst occurs cleanly in the presence of hydrogen peroxide, sodi um hypochlorite or iodosylbenzene as the stoichiometric oxidant. Meso 3,4-c is-isopropylidenedioxy-1-hydroxypyrrolidine gave the corresponding protecte d 3,4-cis-dihydroxypyrroline N-oxide in an enantioenriched fashion for the first time (up to 36% e.e.). (C) 1999 Elsevier Science Ltd. All rights rese rved.