Tuesday, 24 May 2005
724

This presentation is part of: Organic Posters

Facile one pot synthesis of heterocycles from allenes and mechanistic insight on the opening of spirodiepoxides

Stephen D. Lotesta, Sreenivas Katukojvala, Sezgin Kiren, R. R. Sauers, and Lawrence J. Williams. Rutgers University, Piscataway, NJ

New routes to oxazoles, thiazoles, and imidazoles continue to be of interest to the synthetic community, as these moieties are common in pharmacologically active compounds and natural products. In the course of our studies on reactive heterocyclic intermediates, we discovered a direct approach to these heterocycles. Here we report a one pot procedure to heterocycles of type (2) from readily available allenes (1). Experimental and computational data support intramolecular general acid catalyzed spirodiepoxide opening.


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