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Paper | Special issue | Vol 67, No. 2, 2006, pp.721-730
Published online, 18th October, 2005
DOI: 10.3987/COM-05-S(T)69
A Diastereoselective Silver(I) Promoted gem-Dibromocyclopropane Ring Opening Reaction via an Anchimeric Assisted Transannular Benzoate Migration

Matt S. Mortensen, Aaron C. Schmitt, Catherine M. Smith, Eric A. Voight, and George A. O’Doherty*

*Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, U.S.A.

Abstract

A highly diastereoselective synthesis of a protected 4-amino-5,7-dihydroxy-1-bromocyclohept-1-ene was achieved by a silver tosylate promoted gem-dibromocyclopropane ring opening reaction. The target molecule was prepared in only six steps from benzene or four steps from 7,7-dibromo-3-norcarene. The key to this approach was the discovery of a stereoselective transannular benzoate migration, which occurred via tandem anchimeric assistance in a silver(I) promoted gem-dibromocyclopropane ring opening reaction.