Srikrishna, Adusumilli ; Ramasastry, Sripada S. V. (2005) A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone Tetrahedron: Asymmetry, 16 (17). pp. 2973-2979. ISSN 0957-4166
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetasy.2005.07.030
Abstract
Acid catalysed reaction of carvone epoxide 2 resulted in dimeric products 3 and 4, in contrast to the expected ring contraction product. Reaction of β-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: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 48716 |
| Deposited On: | 15 Jul 2011 11:47 |
| Last Modified: | 15 Jul 2011 11:47 |
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