Intramolecular Diels-Alder and Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Reactions of 1,3,4-Oxadiazoles

J. Am. Chem. Soc., 124 (38), 11292 -11294, 2002. 10.1021/ja027533n S0002-7863(02)07533-9
Web Release Date: August 29, 2002

Intramolecular Diels-Alder and Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Reactions of 1,3,4-Oxadiazoles

Gordon D. Wilkie, Gregory I. Elliott, Brian S. J. Blagg, Scott E. Wolkenberg, Danielle R. Soenen, Michael M. Miller, Scott Pollack, and Dale L. Boger*

Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037

Received July 2, 2002

Abstract:

The scope of intramolecular Diels-Alder and a novel tandem Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles is disclosed. In the cases examined, the tandem cycloadditions construct three new rings with formation of four new C-C bonds and set all six stereocenters about a central six-membered ring in a single step including three contiguous and four total quaternary centers without a trace of a second diastereomer.

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