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.
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|
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