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.
Related projects:	Příprava unikátních modulátorů adenylyl cyklázy