DIASTEREOSELECTIVE NUCLEOPHILIC-ADDITION OF ACETYLIDE TO N-BENZYL-2, 3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE NITRONE (BIGN) - STEREODIVERGENT SYNTHESIS OF BETA-HYDROXY-ALPHA-(HYDROXYAMINO)-ACID AND BETA-HYDROXY-ALPHA-AMINO-ACID

Authors
MERINO P FRANCE S MERCHAN FL TEJERO T
Citation
P. Merino et al., DIASTEREOSELECTIVE NUCLEOPHILIC-ADDITION OF ACETYLIDE TO N-BENZYL-2, 3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE NITRONE (BIGN) - STEREODIVERGENT SYNTHESIS OF BETA-HYDROXY-ALPHA-(HYDROXYAMINO)-ACID AND BETA-HYDROXY-ALPHA-AMINO-ACID, Tetrahedron : asymmetry, 8(20), 1997, pp. 3489-3496
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
20
Year of publication
1997
Pages
3489 - 3496
Database
ISI
SICI code
0957-4166(1997)8:20<3489:DNOATN>2.0.ZU;2-0
Abstract
The stereocontrolled nucleophilic addition of lithium trimethylsilyl a cetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylid ene-D-glyceraldehyde, followed by oxidative cleavage of the ensuing pr opargyl hydroxylamines resulted in an efficient stereodivergent synthe sis of fully protected epimeric N-hydroxy alpha-amino esters 8 and 13 as well as the corresponding cw-amino esters 9 and 14. (C) 1997 Publis hed by Elsevier Science Ltd.