Journal of Organic Chemistry 2002-10-04

Rapid syntheses of benzopyrans from o-OBOC salicylaldehydes and salicyl alcohols: a three-component reaction.

Ryan M Jones, Carolyn Selenski, Thomas R R Pettus

Index: J. Org. Chem. 67(20) , 6911-5, (2002)

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Abstract

The Diels-Alder reactions of o-quinone methides generated from OBOC-salicylic aldehydes and alcohols are described, allowing for the synthesis of various substituted benzopyrans. The low temperatures employed for this procedure enable high diastereoselectivity in reactions with beta-substituted o-quinone methides.