Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles

Jie Huang and Alison J. Frontier*
Department of Chemistry, University of Rochester, Rochester, New York 14627
J. Am. Chem. Soc., 2007, 129 (26), pp 8060–8061
DOI: 10.1021/ja0716148
Publication Date (Web): June 8, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, frontier@chem.rochester.edu

Abstract

Abstract Image

A stereoselective Nazarov cyclization/Wagner−Meerwein rearrangement sequence for the synthesis of spirocyclic compounds was developed. While a range of different substrate types engaged in the cyclization/rearrangement sequence, it was found that different substrates underwent different reaction pathways. Depending on the substitution pattern of the substrate, the sequence was terminated by either a hydride shift or the shift of a vinyl or aryl group. It was also possible to install adjacent quaternary stereocenters using this protocol. The efficiency of the Wagner−Meerwein rearrangement was found to be dependent upon both the type and the amount of promoter used to generate the intermediate oxyallyl cation.

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History

  • Published In Issue July 04, 2007
  • Received March 7, 2007

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