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CHINESE CHEMICAL LETTERS · 2016 · IF 1.947

Enzyme-catalyzed direct three-component aza-Diels–Alder reaction using lipase from Candida sp. 99–125

Dong-Hang Yin,Wei Liu,Zhi-Xiang Wang,Xin Huang,Jing Zhang,De-Chun Huang

The direct three-component aza-Diels–Alder reaction was conducted with lipase as a catalyst for the first time. Under the optimized conditions, the aza-Diels–Alder reaction catalyzed by lipase from Candida sp. 99–125 provided the products in moderate to excellent yields. Meanwhile, the endo / exo ratio reached up to 88:12.

研究领域: 生物化学 · 有机合成 · 酶学

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JOURNAL OF ORGANIC CHEMISTRY · 2023 · IF 3.6

Balancing Activity and Stability in Halogen-Bonding Catalysis: Iodopyridinium-Catalyzed One-Pot Synthesis of 2,3-Dihydropyridinones

Yi Li,Yicen Ge,Rui Sun,Xiao Yang,Shipeng Huang,Huajian Dong,Yunyao Liu,Haodan Xue,Xiaoyan Ma,Haiyan Fu,Zeqin Chen

A one-pot cascade reaction for 2,3-dihydropyridinone synthesis was accomplished with 3-fluoro-2-iodo-1-methylpyridinium triflate as the halogen bond catalyst. The desired [4+2] cycloaddition products, bearing aryl, heteroaryl, alkyl, and alicyclic substituents, were successfully furnished in 28–99% yields. Mechanistic investigations proved that a strong halogen-bonding interaction forged between the iodopyridinium catalyst and imine intermediate was essential to dynamically masking the vulnerable C–I bond on the catalyst and accelerating the following aza-Diels–Alder reaction.

CAS / MDL: 50-00-0 54125-02-9

研究领域: 有机化学 · 催化化学

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Enzyme-catalyzed direct three-component aza-Diels–Alder reaction using lipase from Candida sp. 99–125

Balancing Activity and Stability in Halogen-Bonding Catalysis: Iodopyridinium-Catalyzed One-Pot Synthesis of 2,3-Dihydropyridinones