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

Warning

This publication doesn't include Faculty of Economics and Administration. It includes Faculty of Science. Official publication website can be found on muni.cz.

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