Enantioselective Synthesis of 4H-Pyrans Through Organocatalytic Asymmetric Formal [3+3] Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with β-Keto Esters

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• 作者：Zhenting Yue ; Wenbo Li ; Lu Liu ; Cuihong Wang and Junliang Zhang
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：October 6, 2016
• 年：2016
• 卷：358
• 期：19
• 页码：3015-3020
• 全文大小：1397K
• ISSN：1615-4169

文摘

4H-Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2-(1-alkynyl)-2-alken-1-ones and β-keto esters catalyzed by a cyclohexyldiamine-based thiourea-tertiary amine bifunctional catalyst. Under the mild and eco-friendly conditions, a wide range of polysubstituted 4H-pyrans were obtained in moderate yields with good enantioselectivities.