A NEW, STEREOSELECTIVE APPROACH TO PYRROLIDINE-N-OXIDES BY SEQUENTIALCONDENSATION OF SULFONES WITH NITRONES AND REVERSE-COPE-ELIMINATION

Authors
WHEILDON AR KNIGHT DW LEESE MP
Citation
Ar. Wheildon et al., A NEW, STEREOSELECTIVE APPROACH TO PYRROLIDINE-N-OXIDES BY SEQUENTIALCONDENSATION OF SULFONES WITH NITRONES AND REVERSE-COPE-ELIMINATION, Tetrahedron letters, 38(49), 1997, pp. 8553-8556
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
49
Year of publication
1997
Pages
8553 - 8556
Database
ISI
SICI code
0040-4039(1997)38:49<8553:ANSATP>2.0.ZU;2-5
Abstract
Lithiosulfones 10 condense smoothly and highly stereoselectively with nitrones 11 to give unsaturated hydroxylamines 12 which undergo revers e-Cope cyclisations at varying rates leading to pyrrolidine-N-oxidies 13 and 14; the former isomerized slowly to diastereoisomers 20. (C) 19 97 Elsevier Science Ltd.