Please use this identifier to cite or link to this item:
|Title:||The synthesis of fused and spiro annulated carbohydrate structures using copper(I) catalysed intramolecular photoannulation of glucose derivatives.|
|Citation:||ORG BIOMOL CHEM, 2004, 2 (7), pp. 1093-1097|
|Abstract:||Intramolecular [2 + 2] photoannulation catalysed by copper(i)triflate has been applied to a series of carbohydrate derivatives obtained from glucose. Dienes 1a and 1b lead to cyclobutanes 3a and 3b whereas the diastereoisomeric dienes 5a and 5b gave diastereoisomeric products 7a and 7b. These results demonstrate that the reaction is stereospecific. Products 3a and 7a were converted into bromoesters 4 and 9 respectively. The Vasella elimination of 8 lead to the expected bicyclic aldehyde 10 and the ring expanded hydroxy ketone 12. The stereospecific formation of enantiomerically pure spiro annulated carbohydrates 18a and 18b was demonstrated whereas in example 19 no selectivity in the formation of 20 and 21 was observed.|
|Appears in Collections:||Published Articles, Dept. of Chemistry|
Files in This Item:
There are no files associated with this item.
Items in LRA are protected by copyright, with all rights reserved, unless otherwise indicated.