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Short Paper | Regular issue | Vol 87, No. 9, 2013, pp.1903-1916
Published online, 5th August, 2013
DOI: 10.3987/COM-13-12769
Bifunctionalized Allenes. Part X. An Electrophilic Cyclization Protocol for Convenient Highly Regioselective Synthesis of 3-Sulfonylfuran-2(5H)-ones from 2-Sulfonylallenoates

Valerij Ch. Christov,* Ivaylo K. Ivanov, and Ismail E. Ismailov

*Department of Organic Chemistry & Technology, Konstantin Preslavsky University of Shumen, 115, Universitetska str. BG-9712 Shumen, Bulgaria

Abstract

A simple and convenient protocol for the highly regioselective synthesis of 3-sulfonylfuran-2(5H)-ones by electrophilic cyclization reaction of 2-sulfonylallenecarboxylates with neighbouring ester group participation is described. However, the reaction of 2-sulfonylalka-2,3-dien-1-ones with electrophilic reagents proceeded with formation of 2-sulfonylalka-2,4-dien-1-ones by addition-elimination reaction. A possible mechanism involving the cyclization and addition-elimination reaction of 2-sulfonyl-substituted allenic esters and ketones was proposed.