Highly regio and stereoselective hydroxy-directed Diels-Alder reaction.

Abstract

The Diels-Alder reaction has proven to be an invaluable tool in the arsenal of the synthetic organic chemist for the relatively facile construction of cyclic cores. However, the utility of this reaction is not without its shortcomings. Lack of regio and stereoselectivity are two problems that are often encountered with asymmetric dienophiles. Although Lewis acids have been successfully employed to control the selectivity of Diels-Alder reactions involving activated dienophiles, there is little precedent in the literature for their use with dienes containing a tertiary alcohol functionality, due to elimination complications. To this end, a new method has been developed, and reported herein, for the control of both the regio and facial selectivity of the Diels-Alder reaction via a Lewis acid tether to the dienophile directed by the tertiary alcohol on the diene.* *Please refer to dissertation for diagrams.