| KUČERA, Roman, Ondřej HYLSE, Michal BABIAK a Jakub ŠVENDA. Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission. Tetrahedron Letters. OXFORD: Pergamon Press, 2015, roč. 56, č. 45, s. 6171-6173. ISSN 0040-4039. Dostupné z: https://dx.doi.org/10.1016/j.tetlet.2015.09.015. |
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@article{1375990,
author = {Kučera, Roman and Hylse, Ondřej and Babiak, Michal and Švenda, Jakub},
article_location = {OXFORD},
article_number = {45},
doi = {http://dx.doi.org/10.1016/j.tetlet.2015.09.015},
keywords = {Oxirane cleavage; Vinylogous rearrangement; Ring expansion; Ring contraction; Organic synthesis},
language = {eng},
issn = {0040-4039},
journal = {Tetrahedron Letters},
title = {Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission},
url = {http://www.sciencedirect.com/science/article/pii/S0040403915300575},
volume = {56},
year = {2015}
}
TY - JOUR
ID - 1375990
AU - Kučera, Roman - Hylse, Ondřej - Babiak, Michal - Švenda, Jakub
PY - 2015
TI - Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission
JF - Tetrahedron Letters
VL - 56
IS - 45
SP - 6171-6173
EP - 6171-6173
PB - Pergamon Press
SN - 00404039
KW - Oxirane cleavage
KW - Vinylogous rearrangement
KW - Ring expansion
KW - Ring contraction
KW - Organic synthesis
UR - http://www.sciencedirect.com/science/article/pii/S0040403915300575
L2 - http://www.sciencedirect.com/science/article/pii/S0040403915300575
N2 - alpha-Hydroxy-beta-dicarbonyls are known to undergo base-induced rearrangement to alpha-acyloxy carbonyls by a mechanism believed to involve an oxirane C-C bond scission step. Herein, we report the first example of this process in a vinylogous system. An attempt to access the protected form of the putative oxirane intermediate revealed an additional rearrangement pathway that was available to the substrate. Oxirane C-C bond cleavage mechanisms were invoked to explain both isomerizations. (C) 2015 Elsevier Ltd. All rights reserved.
ER -
KUČERA, Roman, Ondřej HYLSE, Michal BABIAK a Jakub ŠVENDA. Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission. \textit{Tetrahedron Letters}. OXFORD: Pergamon Press, 2015, roč.~56, č.~45, s.~6171-6173. ISSN~0040-4039. Dostupné z: https://dx.doi.org/10.1016/j.tetlet.2015.09.015.
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