NEW CARBOHYDRATE-BASED CHIRAL AUXILIARIES IN DIELS-ALDER REACTION

Authors
FERREIRA MLG PINHEIRO S PERRONE CC COSTA PRR FERREIRA VF
Citation
Mlg. Ferreira et al., NEW CARBOHYDRATE-BASED CHIRAL AUXILIARIES IN DIELS-ALDER REACTION, Tetrahedron : asymmetry, 9(15), 1998, pp. 2671-2680
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
15
Year of publication
1998
Pages
2671 - 2680
Database
ISI
SICI code
0957-4166(1998)9:15<2671:NCCAID>2.0.ZU;2-Z
Abstract
The carbohydrate derivatives 1-5 were evaluated as chiral auxiliaries in the Diels-Alder reaction of its acrylate derivatives 6a-e with cycl opentadiene promoted by Lewis acids. Although excellent endo:exo ratio s (98:2) were obtained in many cases, the rr-facial selectivities were from low to moderate (up to 60% d.e.). An effect of noncoordinating s olvents reversing the stereoselectivities of adducts obtained from acr ylates 6a,b was also found. (C) 1998 Elsevier Science Ltd. All rights reserved.