Stereospecificity in Diels–Alder reactions of dienes and dienophiles derived from methyl 4,6-O-benzylidene-α-D-glucopyranoside
- 1 January 1988
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 11,p. 706-707
- https://doi.org/10.1039/c39880000706
Abstract
Conjugated enals (1) and (2) and dienes (3) and (4) derived from methyl 4,6-O-benzylidene-α-D-glucopyranoside underwent highly efficient (yields ranging from 75 to 95%) Diels–Alder reaction with complete facial specificity with butadiene, dimethyl acetylenedicarboxylate, and maleic anhydride leading exclusively to endo adducts with the latter.Keywords
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