Asymmetric Synthesis of 6,6’-Dialkyl and -Diphenyl-2,2’-Biphenyldiols by Using Menthone as a Chiral Template

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Abstract
A general method for the preparation of axially chiral (S)-6,6’-dialkyl- and -diphenyl-2,2’-biphenyldiols are developed. Enantiomerically pure acetal 1, prepared by the stereoselective reaction of 2,2’,6,6’-biphenyltetrol with l-menthone, is converted into bis(triflate) (S)-4 in three steps. Palladium(0)-catalyzed coupling reaction of (S)-4 with organoboron reagents and deprotection of the coupling products afford biphenyldiols (S)-8 of high optical purities.

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