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Issue 12, 1997
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Regio- and stereo-chemical outcomes in the nucleophilic ring cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols

Abstract

Reactions of the mono-epoxy derivatives, 4–7, of the cis-1,2-dihydrocatechols 1 and 2 with various oxygen-, nitrogen-, carbon- and halogen-centred nucleophiles have been studied. In both direct and acid-catalysed processes these epoxides react exclusively by the pathway involving nucleophilic attack at 5a-C of the substrate and such regioselectivity has been exploited in a synthesis of the fluoro-deoxy-conduritol 32. Palladium-catalysed nucleophilic additions to epoxide 4 proceed in the same regiochemical sense (attack at 5a-C) but with overall retention of configuration. A competing process associated with palladium-catalysed addition of phthalimide to epoxide 4 is isomerisation of the substrate to cyclohexenone 41. Product structures have been established by single-crystal X-ray analyses and chemical correlation studies.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 1779-1792
Article type
Paper

Regio- and stereo-chemical outcomes in the nucleophilic ring cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols

M. G. Banwell, N. Haddad, T. Hudlicky, T. C. Nugent, M. F. Mackay and S. L. Richards, J. Chem. Soc., Perkin Trans. 1, 1997, 1779
DOI: 10.1039/A700733G

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