Asymmetric induction of cyclopentadiene in the Diels-Alder reaction on acrylic derivatives of arabinose and ribose O-methylene acetals

Article abstract of DOI:10.1016/S0040-4020(01)88216-8

The acrylates of methyl β-D-arabinopyranoside and methyl β-D-ribofuranoside protected respectively as 3,4- and 2,3-O-methyleneacetals have been used as chiral templates in the asymmetric Diels-Alder reaction with cyclopentadiene. Sugar moieties are very stable towards Lewis acids and the arabinose derivative is very efficient for asymmetric induction.