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4584160 
Journal Article 
Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission 
Kucera, R; Hylse, O; Babiak, M; Svenda, J 
2015 
1 
Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 
56 
45 
6171-6173 
WOS:000363828500002 
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. 
Oxirane cleavage; Vinylogous rearrangement; Ring expansion; Ring contraction; Organic synthesis