Tetrahedron letters

Studies into diastereoselective Dötz benzannulations for the synthesis of axially chiral biaryls

JC Anderson, JW Cran, NP King

Index: Anderson, James C.; Cran, John W.; King, N. Paul Tetrahedron Letters, 2003 , vol. 44, # 42 p. 7771 - 7774

Full Text: HTML

Citation Number: 12

Abstract

A series of racemic chiral ortho substituents on 1-phenylhex-1-yne have been found to control the atroposelective formation of a biaryl from Dötz benzannulation with pentacarbonyl (methoxyphenylmethylene) chromium (0). The results show there is a subtle balance between the chiral ortho substituent controlling atroposelectivity with a dr 3–5: 1 and allowing benzannulation to proceed in yields of 44–67%.