Facile rearrangements of a vinylogous α-hydroxy-β-dicarbonyl substrate involving an apparent oxirane C–C bond scission

Autor:	Ondrej Hylse, Roman Kučera, Michal Babiak, Jakub Švenda
Rok vydání:	2015
Předmět:	010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Drug Discovery Substrate (chemistry) 010402 general chemistry 01 natural sciences Biochemistry Bond cleavage 0104 chemical sciences
Zdroj:	Tetrahedron Letters. 56:6171-6173
ISSN:	0040-4039
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::62f2feb7a0579071d78d4dbde6abbc3d https://doi.org/10.1016/j.tetlet.2015.09.015 Zobrazit plný text záznamu Full Text from ScienceDirect