Asymmetric Dihydroxylation of a Meso-Symmetric Cyclic Diene Using AD-Mix Reagents: A New Enantiocontrolled Route to Conduritol E

Seiichi Takano, Takehiko Yoshimitsu, Kunio Ogasawara

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

The asymmetric dihydroxylation of two symmetric cyclohexa-1,3-diene derivatives, including a meso-symmetric substrate, has been investigated for the first time using the Sharpless AD-mix reagents. Although cyclohexa-1,3-diene itself showed unsatisfactory enantioselectivity, meso-symmetric 1,2-O-benzylidene-cis-cyclohexa-3,5-diene-1,2-diol showed a practical level of enantioselectivity and furnished the optically active diol in good yield. The diol obtained could be transformed into optically pure (+)-conduritol E in good yield, after a single recrystallization. The stereochemical outcome of the dihydroxylation was in harmony with the observations so far reported.

Original languageEnglish
Pages (from-to)54-57
Number of pages4
JournalJournal of Organic Chemistry
Volume59
Issue number1
DOIs
Publication statusPublished - Jan 1 1994
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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