The Cascade Reaction Chemistry of Diazo Compounds with Intentionally Designed Alkene to Access Esterified Heterocycles
Shi-Cui Fang, Shao-Qun Cai, Panpan Li, Zhi‐gang Yang, Jun-Fei Zhao, Hui-Xin Xiao, Yutong Zhou, Xin-Ran Sun, Shuai He, Fang Liu, Wu Liang, Bin Pan, Fei Du
Abstract
Exploration of the cascade reactivity of diazo compounds with alkenes is a challenging and largely unmet goal. Herein, we disclose a light-mediated de novo synthesis of esterified heterocycles under mild conditions. The reaction displays a broad functional group tolerance, including a wide variety of alkenes, diazo compounds, and some bioactive molecules. Importantly, the synthetic appeal was demonstrated for synthesizing indoleamine 2,3-dioxygenase inhibitor analogue, the deethylated derivative of natural product leucomidine C, and the anti-inflammatory agent AN669.
Topics & Concepts
ChemistryDiazoAlkeneNatural productReactivity (psychology)Combinatorial chemistryDerivative (finance)Functional groupCascadeCascade reactionOrganic chemistryCatalysisAlternative medicineFinancial economicsPathologyPolymerMedicineChromatographyEconomicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions