Intermolecular Homopropargyl Alcohol Addition to Alkyne and a Sequential 1,6-Enyne Cycloisomerization with Triazole-Gold Catalyst

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• 作者：Seyedmorteza Hosseyni ; Lukasz Wojtas ; Minyong Li ; Xiaodong Shi
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：March 30, 2016
• 年：2016
• 卷：138
• 期：12
• 页码：3994-3997
• 全文大小：469K
• ISSN：1520-5126

文摘

While gold-catalyzed homopropargyl alcohol cyclization is a known process, a triazole-gold catalyst prevented the intramolecular cyclization in the presence of terminal alkynes. As a result, an intermolecular addition to an alkyne was achieved. A sequential 1,6-enyne cycloisomerization gave the unusual 2,3-dihydrooxepine, which revealed another new reaction path. Diels–Alder reaction of oxepine followed by a 1,3-alkoxyl shift gave hydrobezofuran derivatives in high yields. Diasterioselective reaction of homopropargyl alcohol to final product enabled one-step formation of five stereogenic centers with excellent enantiomeric selectivity.