Kinetic Resolution of Mono‐ and Bicyclic Diels‐Alder Adducts via Sharpless Asymmetric Dihydroxylation.

Simple mono- and bicyclic olefins, readily available by the Diels-Alder methodology, are subjected to osmium-catalyzed asymmetric dihydroxylation with the aim to achieve kinetic resolution of the Diels-Alder adducts. The stereoselectivity factor s varies from 1.1 to 2.5. An effective procedure is developed to reconvert the cis-vicinal diols into the corresponding alkenes.