Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

D. R. Boyd, N. D. Sharma, M. Kaik, M. Bell, M. V. Berberian, P.B.A. McIntyre, B. Kelly, C. Hardacre, P. J. Stevenson, C. C. R. Allen

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9 Citations (Scopus)

Abstract

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.
Original languageEnglish
Pages (from-to)2455-2465
Number of pages11
JournalAdvanced Synthesis & Catalysis
Volume353
Issue number13
DOIs
Publication statusPublished - Sep 2011

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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