Dehydrative ReO-Catalyzed Approach to Dihydropyran Synthesis.

Org Lett

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.

Published: December 2020

Monoallylic 1,3- and 1,5-diols undergo ReO-mediated ionization to form allylic cations that engage in cyclization reactions to form dihydropyran products. The reactions give the 2,6--stereoisomer as the major products as a result of minimizing steric interactions in a boat-like transition state. The results of these studies are consistent with cationic intermediates, with an intriguing observation of stereochemical retention in one example.

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http://dx.doi.org/10.1021/acs.orglett.0c03526DOI Listing

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