A STRAIGHTFORWARD SYNTHESIS OF (2S,3R)-3-HYDROXYPROLINE AND TRANS-(2R,3S)-2-HYDROXYMETHYL-3-HYDROXYPYRROLIDINE

Authors
DELLUOMO N DIGIOVANNI MC MISITI D ZAPPIA G DELLEMONACHE G
Citation
N. Delluomo et al., A STRAIGHTFORWARD SYNTHESIS OF (2S,3R)-3-HYDROXYPROLINE AND TRANS-(2R,3S)-2-HYDROXYMETHYL-3-HYDROXYPYRROLIDINE, Tetrahedron : asymmetry, 7(1), 1996, pp. 181-188
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
1
Year of publication
1996
Pages
181 - 188
Database
ISI
SICI code
0957-4166(1996)7:1<181:ASSO(A>2.0.ZU;2-#
Abstract
A stereocontrolled synthesis of (2S,3R)-3-hydroxyproline 1, and trans- (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine 2 has been achieved in 21 % and 38% yield via the homochiral 4,5-disubstituted oxazolidin-2-one 3. The trans relationship in 2 has been introduced by a modified Mitsu nobu reaction.