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Construction of Functionalized 2H-Pyran-2-ones via N-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Alkynyl Esters with Enolizable Ketones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-01-25 , DOI: 10.1021/acs.joc.2c02392 Zheng Liang 1 , Jibin Li 1 , Lei Wang 1 , Zexuan Wei 1 , Jiahui Huang 1 , Xinrui Wang 1 , Ding Du 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-01-25 , DOI: 10.1021/acs.joc.2c02392 Zheng Liang 1 , Jibin Li 1 , Lei Wang 1 , Zexuan Wei 1 , Jiahui Huang 1 , Xinrui Wang 1 , Ding Du 1
Affiliation
A new synthesis of functionalized 2H-pyran-2-ones has been developed through N-heterocyclic carbene-catalyzed formal [3 + 3] annulation of alkynyl esters with enolizable ketones. The key to the success of this protocol relies on the use of an NHC instead of a tertiary amine as the catalyst. This protocol also features a broad substrate scope and mild metal-free conditions, offering simple and rapid access to the target molecules in a highly regioselective manner.
中文翻译:
N-杂环卡宾催化 [3 + 3] 炔基酯与烯醇化酮成环反应构建功能化 2H-吡喃-2-酮
通过 N-杂环卡宾催化的炔基酯与可烯醇化酮的正式 [3 + 3] 环化,开发了功能化 2 H -pyran-2-ones的新合成方法。该协议成功的关键在于使用 NHC 而不是叔胺作为催化剂。该协议还具有广泛的底物范围和温和的无金属条件,以高度区域选择性的方式提供对目标分子的简单快速访问。
更新日期:2023-01-25
中文翻译:
N-杂环卡宾催化 [3 + 3] 炔基酯与烯醇化酮成环反应构建功能化 2H-吡喃-2-酮
通过 N-杂环卡宾催化的炔基酯与可烯醇化酮的正式 [3 + 3] 环化,开发了功能化 2 H -pyran-2-ones的新合成方法。该协议成功的关键在于使用 NHC 而不是叔胺作为催化剂。该协议还具有广泛的底物范围和温和的无金属条件,以高度区域选择性的方式提供对目标分子的简单快速访问。