PDF herunterladen
Synlett 1995; 1995(3): 283-284
DOI: 10.1055/s-1995-4938
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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