Elsevier

Tetrahedron Letters

Volume 46, Issue 32, 8 August 2005, Pages 5329-5332
Tetrahedron Letters

Stereoselective synthesis of spiroannulated cyclopentenones by the Pauson–Khand reaction on carbohydrate derived enynes

https://doi.org/10.1016/j.tetlet.2005.06.013Get rights and content

Abstract

The stereoselective synthesis of spiroannulated cyclopentenones by the Pauson–Khand reactions on hexose and pentose derived enynes was achieved under carbon monoxide free conditions using a stoichiometric quantity of Co2(CO)8. The cobalt complex of the alkyne was cleaved using dimethoxyethane–acetonitrile at 85 °C to furnish spiroannulated cyclopentenones in 75–94% yields.

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Acknowledgements

S.H. thanks the Director, NCL (MLP003326) and DST, New Delhi (SR/S1/OC-06/2004), for financial support. S.H. is grateful for the encouragement of Dr. K. N. Ganesh. S.K.M. acknowledges the fellowship from UGC-New Delhi.

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