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 |
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Publication: | Tetrahedron: Asymmetry |
Publisher: | Pergamon-Elsevier Science Ltd |
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.ac.in/id/eprint/3888 |
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