Highly-substituted 2-isoxazolines, particularly those that can be formed stereoselectively, are coveted as synthetic intermediates and synthesis targets alike. Intramolecular nitrile oxide cycloadditions (INOC) present an attractive approach to 2-isoxazolines, and the constraints of cyclic transition states and the resulting bicyclic systems are conducive to stereoselective reactions.  Literature reports of INOC where the dipolarophile is tethered to the nitrile oxide via an ester are few, and those that have appeared have attained only minimal success.  In our laboratories, a method for fruitful ester-tethered INOC has been explored.  The scope, limitations, and stereochemical course of this INOC will be discussed, as well as synthetic applications for the fused bicyclic system that results.

Construction of a fused bicyclic system via ester-tethered intramolecular nitrile oxide cycloaddition

239th National Meeting (2010)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.