Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission

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Authors

KUČERA Roman HYLSE Ondřej BABIAK Michal ŠVENDA Jakub

Year of publication 2015
Type Article in Periodical
Magazine / Source Tetrahedron Letters
MU Faculty or unit

Faculty of Science

Citation
Web http://www.sciencedirect.com/science/article/pii/S0040403915300575
Doi http://dx.doi.org/10.1016/j.tetlet.2015.09.015
Field Organic chemistry
Keywords Oxirane cleavage; Vinylogous rearrangement; Ring expansion; Ring contraction; Organic synthesis
Description 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.
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