期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 19, 页码 7625-7630出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo801406p
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资金
- Ministry of Education of China [108044]
- National Natural Science Foundation of China [20672019]
- Department of Science and Technology of Jilin [20070549]
- Science Foundation for Young Teacher of Northeast Normal University [20070308]
A route to 2,3,4-trisubstituted furan derivatives based on a [3 + 2] annulation of functionalized allylic sulfoxides and aldehydes is described. In this strategy, the precursors of allylic sulfoxides 4, allylic sulfides 3, were synthesized via a thiomethylation reaction of an alpha-EWG ketene-S,S-acetal 1 (EWG: electron-withdrawing group), formaldehyde, and a thiol 2 in high to excellent yields. Allylic sulfoxides 4 were prepared by a highly regioselective oxidation of 3, using m-chloroperoxybenzoic acid as oxidant. Thus, starting from these readily available sulfoxides 4, 2-alkylthio-3,4-disubstituted furans 6 were efficiently constructed via the [3 + 2] annulation reaction of 4 with aldehydes 5 under mild conditions. Further replacement of the 2-alkylthio group of 6 with amines led to the formation of 2-amino-3,4-disubstituted furan derivatives 7.
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