Tetrahedron: Asymmetry

[9, 9′] Bi [naphtho (2, 1-b) furanyl]-8, 8′-diol, a furo-fused BINOL derivative: synthesis, resolution and determination of absolute configuration

AV Karnik, SP Upadhyay, MG Gangrade

Index: Karnik, Anil V.; Upadhyay, Sunil P.; Gangrade, Manish G. Tetrahedron Asymmetry, 2006 , vol. 17, # 8 p. 1275 - 1280

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Citation Number: 6

Abstract

A high yielding synthetic protocol was employed in order to achieve the placement of a furan ring at the most sterically crucial position of BINOL to obtain [9, 9′] bi [naphtha (2, 1-b) furanyl]-8, 8′-diol. The racemate was resolved and the configuration of one of the enantiomers was found by single crystal X-ray analysis of a Mosher's acid diester derivative. This furo-fused BINOL derivative exhibited modified steric and electronic properties.