The Copper(I) Catalysed [2 + 2] Intramolecular Photoannulation of Carbohydrate Derivatives

David J. Holt; William D. Barker; Paul R. Jenkins; Subrata Ghosh; David R. Russell; John Fawcett

doi:10.1055/s-1999-3120

Synlett 1999; 1999(S1): 1003-1005
DOI: 10.1055/s-1999-3120

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The Copper(I) Catalysed [2 + 2] Intramolecular Photoannulation of Carbohydrate Derivatives

David J. Holt^* , William D. Barker, Paul R. Jenkins, Subrata Ghosh, David R. Russell, John Fawcett

^*Department of Chemistry, Leicester University, Leicester, LE1 7RH, UK; Fax +44(1 16)2 52 37 89; E-mail: for PRJ: kin@le.ac.uk

Abstract

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Carbohydrate derivatives 1a, 1b, 3a and 3b have been subjected to copper(I) catalysed photoannulation to produce tetracyclic products 2a, 2b, 4a and 4b respectively as single enantiomers. The same reaction carried out on substrates 5a and 5b leads stereoselectively to the spiro products 6a and 6b respectively. Photoannulation of substrate 7 gave an approximate 1 : 1 mixture of spiro products 8 and 9. A mechanistic rationalisation of these results is proposed.

annulation - carbohydrates - copper - cycloadditions - photochemistry

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