ENANTIODIVERGENT SYNTHESIS OF 2-HYDROXYMETHYL-3-HYDROXY-4-NITRO-PYRROLIDINES THROUGH TANDEM MICHAEL-HENRY REACTION USING L-SERINE AS THE CHIRAL EDUCT

Authors
BARCO A BENETTI S DERISI C POLLINI GP ROMAGNOLI R ZANIRATO V
Citation
A. Barco et al., ENANTIODIVERGENT SYNTHESIS OF 2-HYDROXYMETHYL-3-HYDROXY-4-NITRO-PYRROLIDINES THROUGH TANDEM MICHAEL-HENRY REACTION USING L-SERINE AS THE CHIRAL EDUCT, Tetrahedron letters, 37(42), 1996, pp. 7599-7602
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
42
Year of publication
1996
Pages
7599 - 7602
Database
ISI
SICI code
0040-4039(1996)37:42<7599:ESO2>2.0.ZU;2-H
Abstract
By utilizing L-serine, both enantiomers of all trans a-hydroxymethyl 3 -hydroxy-4-nitro-pyrrolidine were efficiently prepared through tandem Michael-Henry methodology. Their stereochemistry has been assigned thr ough conversion of one of them to trans 2-hydroxymethyl-3-hydroxypyrro lidine, a naturally occurring compound recently isolated from Castanos permum australe. Copyright (C) 1996 Elsevier Science Ltd