Holt, David J. ; Barker, William D. ; Jenkins, Paul R. ; Ghosh, Subrata ; Russell, David R. ; Fawcett, John (1999) The copper(I) catalyzed [2 + 2] intramolecular photoannulation of carbohydrate derivatives Synlett, 1999 (S1). pp. 1003-1005. ISSN 0936-5214
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Official URL: http://www.thieme-connect.com/ejournals/abstract/s...
Related URL: http://dx.doi.org/10.1055/s-1999-3120
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
| Keywords: | Annulation; Carbohydrates; Copper; Cycloadditions; Photochemistry |
| ID Code: | 12369 |
| Deposited On: | 10 Nov 2010 06:21 |
| Last Modified: | 14 Feb 2011 04:21 |
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