Diels−Alder Approach to Tetra-ortho-Substituted Biaryls Employing Propargylic Tertiary Alcohols as Dienophiles

Bradley O. Ashburn and Rich G. Carter*
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331 rich.carter@oregonstate.edu
J. Org. Chem., 2007, 72 (26), pp 10220–10223
DOI: 10.1021/jo070812e
Publication Date (Web): June 29, 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.

Abstract

Abstract Image

The efficient synthesis of a series of tetra-ortho-substituted biaryls is described utilizing a Diels−Alder reaction between propargylic tertiary alcohols and cyclic oxygenated dienes. The successful resolution of one of the biaryls is achieved through derivatization with menthyl chloroformate followed by crystallization. The menthyl carbamate is cleaved under basic conditions to reveal enantiomerically pure biaryl compounds.

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History

  • Published In Issue December 21, 2007
  • Received April 17, 2007

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