Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters

Abstract

The capture of selected 1-alkenesulfinyl chlorides with furan-tethered alcohols leads to the formation of diene-tethered 1-alkenesulfinate esters. The esters can spontaneously or with Lewis acid treatment undergo an IMDA reaction to form exo adducts with very high diastereoselectivity. Computational predictions using density functional theory indicate the preferred transition state for cyclization and find little preference for the sulfinyl configuration in the products.