Diastereoselective, Zinc-Catalyzed Alkynylation of 伪-Bromo Oxocarbenium Ions

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• 作者：Tatsiana Haidzinskaya ; Hilary A. Kerchner ; Jixin Liu ; Mary P. Watson
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：17
• 期：15
• 页码：3857-3859
• 全文大小：294K
• ISSN：1523-7052

文摘

We have developed a bromination/alkynylation sequence that enables efficient transformation of simple cyclic enol ethers to difunctionalized products. The success of this strategy relies on a highly diastereselective, zinc-catalyzed addition of terminal alkynes to 伪-bromo oxocarbenium ions, formed in situ via ionization of acetal precursors. Using this method, trans-伪-alkynyl-尾-halo pyran and furan derivatives can be prepared with high diastereoselectivity and excellent functional group tolerance.