A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone
Publication type: Journal Article
Publication date: 2005-09-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
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.
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Srikrishna A., Ramasastry S. A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone // Tetrahedron Asymmetry. 2005. Vol. 16. No. 17. pp. 2973-2979.
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Srikrishna A., Ramasastry S. A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone // Tetrahedron Asymmetry. 2005. Vol. 16. No. 17. pp. 2973-2979.
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TY - JOUR
DO - 10.1016/j.tetasy.2005.07.030
UR - https://doi.org/10.1016/j.tetasy.2005.07.030
TI - A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone
T2 - Tetrahedron Asymmetry
AU - Srikrishna, Adusumilli
AU - Ramasastry, S.S.V.
PY - 2005
DA - 2005/09/01
PB - Elsevier
SP - 2973-2979
IS - 17
VL - 16
SN - 0957-4166
SN - 1362-511X
ER -
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@article{2005_Srikrishna,
author = {Adusumilli Srikrishna and S.S.V. Ramasastry},
title = {A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone},
journal = {Tetrahedron Asymmetry},
year = {2005},
volume = {16},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tetasy.2005.07.030},
number = {17},
pages = {2973--2979},
doi = {10.1016/j.tetasy.2005.07.030}
}
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MLA
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Srikrishna, Adusumilli, and S.S.V. Ramasastry. “A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone.” Tetrahedron Asymmetry, vol. 16, no. 17, Sep. 2005, pp. 2973-2979. https://doi.org/10.1016/j.tetasy.2005.07.030.