Gold(I)-Catalyzed Formal [2+2+2] Cycloaddition of Activated Alkynes and Carbonyls: One-Pot Synthesis of 2H-Pyrans
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Title
- Gold(I)-Catalyzed Formal [2+2+2] Cycloaddition of Activated Alkynes and Carbonyls: One-Pot Synthesis of 2H-Pyrans
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Author(s)
- Sung, Dan Bi; Lee, Jong Seok
- KIOST Author(s)
- Sung, Dan Bi(성단비); Lee, Jong Seok(이종석)
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Alternative Author(s)
- 성단비; 이종석
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Publication Year
- 2023-08-13
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Abstract
- The 2H-pyran is the structural motif embedded in many natural products and usually employed as a key intermediate in the synthesis of natural products and pharmaceutical molecules. While methods for the synthesis of dihydropyrans and tetrahydropyrans have been extensively explored, synthesis of stable 2H-pyrans remains an elusive challenge in current organic synthesis. This is because of the intrinsic instability of 2H-pyrans caused by an equilibrium with 1-oxatrienes via the electrocyclic ring-opening reactions. In this presentation, we describe an efficient one-pot synthesis of highly substituted 2H-pyrans using gold(I) pre-catalyst in combination with a metal triflate as a n activator and another metal triflate as an accelerator. Reactions of linear, cyclic ketones, and aldehydes with various activated alkynes under the above condition provided the corresponding 2H-pyrans in excellent regioselectivity. The newly developed synthetic method constitutes one of the first reports of gold(I)-catalyzed formal [2+2+2] cycloaddition between one unit of a carbonyl compound and two units of an activated alkyne. This method provides a straightforward and general access to various highly substituted 2H-pyrans by applying a combination of a carbonyl compound and an activated alkyne under a mild reaction condition.
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/44847
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Bibliographic Citation
- ACS FALL 2023: Harnessing the Power of Data, 2023
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Publisher
- ACS (American Chemistry of Society)
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Type
- Conference
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Language
- English
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