Theoretical Analysis of a Three-Component Reaction between Two Diazo Compounds and a Hydroxylamine Derivative: Mechanism, Enantioselectivity, and Effect of Cooperative Catalysis

Qi, Simeng; Ma, Ji; Yan, Guowei; Kirillov, Alexander M.; Yang, Lizi; Fang, Ran

doi:10.1021/acs.joc.3c02061

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2024

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Cited by 5 publications

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Silver/Segphos‐Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition for the Enantioselective Synthesis of Pyrrolidine Spirooxindoles

Ma,

Dang,

et al. 2024

Eur J Org Chem

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Enantioselective synthesis of chiral heterocyclic derivatives is an important and challenging topic in the field of synthetic chemistry. In this work, a silver‐catalyzed asymmetric 1,3‐dipolar cycloaddition of glycine iminoesters with 3‐isopropylidene‐2‐oxindoles was developed. The DTBM‐Segphos‐induced spirooxindole cycloaddition reaction was used to synthesize a range of stereodivergent alkyl‐substituted 3‐methylene‐2‐oxindoles, achieving excellent enantioselectivities (up to 99 % ee), good diastereoselectivities (up to 20 : 1 dr), and high yields under mild reaction conditions. Computational insights from DFT calculations indicate that the Michael addition step is crucial in determining the reaction rate and enantioselectivity.

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