NAPHTHYL 3,4,6-TRI-O-METHYL-BETA-D-GLUCOPYRANOSIDE AS A CHIRAL AUXILIARY IN AN ASYMMETRIC 1,4-ADDITION REACTION

Authors
CHIAPPE C LOMORO G MUNFORTE P
Citation
C. Chiappe et al., NAPHTHYL 3,4,6-TRI-O-METHYL-BETA-D-GLUCOPYRANOSIDE AS A CHIRAL AUXILIARY IN AN ASYMMETRIC 1,4-ADDITION REACTION, Tetrahedron : asymmetry, 8(14), 1997, pp. 2311-2317
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
14
Year of publication
1997
Pages
2311 - 2317
Database
ISI
SICI code
0957-4166(1997)8:14<2311:N3AACA>2.0.ZU;2-V
Abstract
Naphthyl 3,4,6-tri-O-methyl-beta-D-glucopyranoside, easily synthesized from tri-O-acetyl-D-glucal, has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high faci al diastereoselection (>95%) was obtained. No diastereoselection was o bserved when 1,3,4,6-tetra-O-methyl-beta-D-glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account ste ric shielding and pi-stacking effects, is proposed on the basis of the observed results. (C) 1997 Elsevier Science Ltd.