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

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.

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(S)-(+)-[9,9′]Bi[naphtho(2,1-b)furanyl]-8,8′-diolC24H14O4Ee = 99.1%[α]58925=+110 (c 1, THF)Source of chirality: resolutionAbsolute configuration: S