Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions
Тип публикации: Journal Article
Дата публикации: 1994-01-01
SCImago Q3
WOS Q2
БС2
SJR: 0.36
CiteScore: 3.7
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
The 2-oxonia Cope rearrangement is shown to play an important role in Lewis acid-induced π-cyclization reactions of a variety of methyl 2-acetoxy-2-(3-alken-1-oxy)acetates to 5- and 6-membered ring ethers. The influence of this [3,3]-sigmatropic rearrangement on the regio- and stereochemical outcome of the cyclization is evaluated by studying three types of substrates, namely (1) four chain-substituted precursors, (2) three silicon-substituted precursors (allyl- and vinylsilanes) and (3) two enantiopure precursors. Controlling factors are the nature of the π-nucleophile and the substitution pattern of the oxycarbenium ion intermediate. The absolute stereochemistry is retained in the cyclization of the enantiopure substrates.
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Lolkema L. D. M. et al. Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions // Tetrahedron. 1994. Vol. 50. No. 24. pp. 7129-7140.
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Lolkema L. D. M., Semeyn C., Ashek L., Hiemstra H., Speckamp W. Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions // Tetrahedron. 1994. Vol. 50. No. 24. pp. 7129-7140.
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TY - JOUR
DO - 10.1016/S0040-4020(01)85239-X
UR - https://doi.org/10.1016/S0040-4020(01)85239-X
TI - Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions
T2 - Tetrahedron
AU - Lolkema, Lucie D M
AU - Semeyn, Cindy
AU - Ashek, Loulou
AU - Hiemstra, H.
AU - Speckamp, W.Nico
PY - 1994
DA - 1994/01/01
PB - Elsevier
SP - 7129-7140
IS - 24
VL - 50
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1994_Lolkema,
author = {Lucie D M Lolkema and Cindy Semeyn and Loulou Ashek and H. Hiemstra and W.Nico Speckamp},
title = {Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions},
journal = {Tetrahedron},
year = {1994},
volume = {50},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(01)85239-X},
number = {24},
pages = {7129--7140},
doi = {10.1016/S0040-4020(01)85239-X}
}
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MLA
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Lolkema, Lucie D. M., et al. “Studies on the role of the 2-oxonia Cope rearrangement in pi-cyclizations of alpha-methoxycarbonyl oxycarbenium ions.” Tetrahedron, vol. 50, no. 24, Jan. 1994, pp. 7129-7140. https://doi.org/10.1016/S0040-4020(01)85239-X.
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