期刊
HETEROCYCLES
卷 87, 期 9, 页码 1903-1916出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-13-12769
关键词
2-Sulfonylallenecarboxylate; 3-Sulfonylfuran-2(5H)-one; Neighbouring Group Participation; 2-Sulfonylalka-2,3-, and-2,4-dien-1-ones
资金
- Research Fund of the Konstantin Preslavsky University of Shumen [RD-08-243/2013]
- National Research Fund of Bulgaria [DRNF-02-13/2009]
- Human Resources Development Operational Programme of the European Union [BG051PO001-3.3.06-0003/2012]
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.
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