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A facile regioselective construction of spiro epoxy-bridged tetrahydropyranone frameworks

Muthusamy, S and Babu, Arulananda S and Nethaji, M (2003) A facile regioselective construction of spiro epoxy-bridged tetrahydropyranone frameworks. In: Tetrahedron, 59 (41). pp. 8117-8127.

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Official URL: http://dx.doi.org/10.1016/j.tet.2003.08.041


Investigations on the reactivity profile of the transient five-membered-ring cyclic carbonyl ylides, generated from alpha-diazo ketones, in the presence of the C=O group of various simple ketones and symrnetrical/unsymmetrical 1,2-diones were carried out. The reaction of alpha-diazo ketones with 1,2-naphthoquinone furnished interesting diastereomeric cycloadducts in which both the C=O groups acted as dipolarophilic sites. The similar reaction in the presence of several isatin derivatives afforded novel spiro dioxa-bridged indole derivatives as a mixture of diastereomers. The single crystal X-ray structure analysis manifestly revealed the mode of cycloaddition and the stereochemistry of two of the diastereomers. A diverse set of novel spiro epoxy-bridged tetrahydropyranone frameworks have been constructed in good yield via the tandem cyclization-cycloaddition of alpha-diazo ketones with the C=O group as heterodipolarophile in a regioselective manner. (C) 2003 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: carbonyl ylides;cycloaddition;α-diazo ketones;diones;rhodium (II) acetate catalyst;spiro compounds
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 03 Aug 2011 09:03
Last Modified: 03 Aug 2011 09:03
URI: http://eprints.iisc.ac.in/id/eprint/39706

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