Diels-Alder Approach to Tetra-ortho-Substituted
Biaryls Employing Propargylic Tertiary Alcohols
as Dienophiles
Bradley O. Ashburn andRich G. Carter*
Department of Chemistry, Oregon State University,
153 Gilbert Hall, Corvallis, Oregon 97331
rich.carter@oregonstate.edu
Received April 17, 2007
Abstract:
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.
