Skeletal transformation of α-pyrones having electron-withdrawing groups at 3, 5-positions into ring-fused dihydrofurans. Issue 46 (18th November 2015)

• Record Type: Journal Article
• Authors: Tanaka, Toru; Miura, Takuya; Inoue, Shoki; Iwasaki, Hiroki; Ozeki, Minoru; Kojima, Naoto; Yamashita, Masayuki
• Is Part Of: Tetrahedron letters. Volume 56:Issue 46(2015)
• Page Start: 6327
• Page End: 6331
• Publication Date: 2015-11-18
• Subjects: Dihydrofuran -- Ylide -- α-Pyrone -- Domino reaction -- 1-Methylthiopyran-1-oxide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A skeletal transformation of α-pyrones having electron-withdrawing groups at the 3, 5-positions into dihydrofurans was developed. Using dimethylsulfoxonium methylide as the methylene-transfer reagent, the α-pyrones were converted into dihydrofurans as major products and 1-methylthiopyran-1-oxides as minor products. The selectivity of the dihydrofuran formation was improved by optimizing the reaction conditions.