Tin triflate promoted synthesis of bicyclic and tricyclic sulfonyl dihydropyrans

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• 作者：Chieh-Kai Chan ; Yu-Hsin Chen ; Meng-Yang Chang ; ^{mychang@kmu.edu.tw" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Tin triflate ; β-Ketosulfones ; Carbocyclization ; Dihydropyrans
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：18 August 2016
• 年：2016
• 卷：72
• 期：33
• 页码：5121-5131
• 全文大小：653 K

文摘

Tin triflate-promoted one-pot intramolecular annulation of α-geranyl or α-farnesyl β-ketosulfones 3–4 affords the respective bicyclic or tricyclic sulfonyl dihydropyrans 5–6 in moderate to good yields via a cascade cation-olefin-carbonyl carbocyclization process. The starting materials 3 and 4 were obtained by K₂CO₃-mediated α-geranylation or α-farnesylation of β-ketosulfones 1 with bromides 2a or 2b. The structures of the key products were confirmed by X-ray crystallography.