Synthesis of γ-sulfonyl δ-lactones and β-sulfonyl styrenes

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• 作者：Chieh-Kai Chan^a ; Yu-Hsin Chen^a ; Ru-Ting Hsu^b ; ^{ruting@ms.szmc.edu.tw} ; Meng-Yang Chang^a ; ^{mychang@kmu.edu.tw}
• 关键词：β-Ketosulfones ; Lactones ; Styrenes
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：5 January 2017
• 年：2017
• 卷：73
• 期：1
• 页码：46-54
• 全文大小：735 K
• 卷排序：73

文摘

A facile route to the synthesis of γ-sulfonyl lactones 5 and β-sulfonyl styrenes 6 has been developed, achieving moderate to good yields via the (1) NaH mediated Michael addition of β-ketosulfones 3 and methyl acrylate in refluxing THF and (2) NaBH4 mediated stereoselective reduction/lactonization of δ-ketoesters 4 in boiling MeOH, or (3) boron trifluoride etherate mediated ring-opening of lactones 5 in MeOH at reflux.