Diels-Alder reaction of sugar-derived cyclic dienophiles with cyclopentadiene. Factors affecting the reactivity and stereoselectivity
[formula: see text] A sugar-derived cyclic dienophile showed a high exo and face selectivity in the Diels-Alder reaction with cyclopentadiene. Structural modifications on the dienophile structure were made, and the outcomes of the cycloaddition reactions were investigated. These results and the spectroscopic data recorded within a series of analogues were used to analyze the factors affecting the reactivity and exo selectivity.
Pellegrinet
SC
Instituto de Quimica Organica de Sintesis, Facultad de Ciencias Bioquimicas y Farmaceuticas, Universidad Nacional de Rosario-CONICET, Argentina.
Spanevello
RA