Axial chirality control by 2,4-pentanediol or its analogue as a simple chiral linking bridge. Highly diastereodifferentiating homocoupling of a 1-lithio-2-naphthyl ether

Abstract

Diastereodifferentiating oxidative homocoupling of 1-lithio-2-naphthyl ether linked by optically active 2,4-pentanediol or 1,3-diphenyl-1,3-propanediol gave 2,2'binaphthyl ether of over 99% diastereomeric excess. By elimination of the chiral auxiliary from the product, enantiomerically pure binaphthol was obtained in good yield.