π-Facial selectivity in Diels–Alder reactions of C-2-vinyl glycals. Stereocontrolled route to annulated C-glycopyranosides
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 11,p. 823-825
- https://doi.org/10.1039/c39900000823
Abstract
An allylic methoxy substituent at C-3 in C-2 vinyl glycals (1b,c) induces complete antiπ-facial selectivity in the thermal Diels–Alder reaction with malefic anhydride; in contrast, products resulting from anti and syn approaches are observed when linear acetylenic compounds are employed as dienophiles; the latter adducts readily aromatize to afford a mixture of products with the pyranose ring unchanged (8) and opened (9).Keywords
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