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A novel boron trifluoride etherate mediated deep-seated rearrangement of an \alpha,\beta-epoxyketone

Srikrishna, Adusumilli and Ramasastry, Sripada SV (2005) A novel boron trifluoride etherate mediated deep-seated rearrangement of an \alpha,\beta-epoxyketone. In: Tetrahedron: Asymmetry, 16 (17). pp. 2973-2979.

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Abstract

Acid catalysed reaction of carvone epoxide 2 resulted in dimericproducts 3 and 4, in contrast to the expected ring contraction product.Reaction of \beta-methylcarvone epoxides 8 and 11 with acids furnished 2-acetyl-4-isopropenylcyclopentanones 9 and 14 containing a stereodefined quaternary carbon atom. On the other hand, the reaction of epoxides 8 and 11 with boron trifluoride etherate lacks the stereoselectivity and in addition, anti-epoxide 8 furnished lactone 18 via an unusual deep seated rearrangement.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elsevier.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Oct 2005
Last Modified: 19 Sep 2010 04:20
URI: http://eprints.iisc.ernet.in/id/eprint/3888

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