STEREOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED CIS-3-(ALPHA-HYDROXYETHYL)-PYRROLIDINE-2-ONES

Authors
BARTELS A JONES PG LIEBSCHER J
Citation
A. Bartels et al., STEREOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED CIS-3-(ALPHA-HYDROXYETHYL)-PYRROLIDINE-2-ONES, Tetrahedron : asymmetry, 8(10), 1997, pp. 1545-1549
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
10
Year of publication
1997
Pages
1545 - 1549
Database
ISI
SICI code
0957-4166(1997)8:10<1545:SSO4C>2.0.ZU;2-Y
Abstract
Michael-addition of nitromethane anion to 5-ylidene-1,3-dioxane-4-ones 2 gives high yields of 5-(beta-nitroalkyl)-1,3-dioxane-4-ones 3 and 4 with a preponderance of 3 (re-attack). Hydrogenation of the products in the presence of Raney-Ni affords optically active 4-substituted cis -3-(alpha-hydroxyethyl)-pyrrolidine-2-ones 6. (C) 1997 Elsevier Scienc e Ltd.