Synthesis and Reactions of Enantiopure Substituted Benzene cis-Hexahydro-1,2-diols

Derek Boyd, Narain Sharma, Victoria Berberian, K.S. Dunne, Christopher Hardacre, Magdalena Kaik, B. Kelly, John Malone, S.T. McGregor, Paul Stevenson

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Enantiopure cis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed cis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding cis-hexahydro-12-diol derivatives by catalytic hydrogenation via their cis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the cis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene cis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure cis-hexahydro-1,2-diol diastereoisomers, to desymmetrise a meso-cis-hexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.
Original languageEnglish
Pages (from-to)855-868
Number of pages14
JournalAdvanced Synthesis & Catalysis
Volume352
Issue number5
Early online date12 Mar 2010
DOIs
Publication statusPublished - 22 Mar 2010

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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