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Synlett 1995; 1995(3): 283-284
DOI: 10.1055/s-1995-4938
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Asymmetric Synthesis of 6,6’-Dialkyl and -Diphenyl-2,2’-Biphenyldiols by Using Menthone as a Chiral Template

Toshiro Harada* , Tetsuya Yoshida, Atsushi Inoue, Masahiro Takeuchi, Akira Oku1
  • *Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606, Japan
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Publication Date:
31 December 2000 (online)

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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.

asymmetric synthesis - axial chirality - 2,2’-biphenyldiols - palladium(0)-catalyzed cross coupling reaction - organoboron reagents

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