An Easy Access to the Synthesis of Sugar‐Based <i>N</i>‐Methyl‐Pyrrolidine via [3 + 2] Cycloaddition Methodology

A Ru(II)/iminium cocatalyzed asymmetric formal [3 + 1 + 1] cycloaddition reaction of diazoacetophenones, anilines, and enals is disclosed to construct multisubstituted pyrrolidines in one step with excellent diastereoselectivity and enantioselectivity. The reaction mechanism was postulated as a successful trapping of Ru(II)-associated ammonium ylides via a selective 1,4-addition to chiral amine activated enals followed by a tandem aza-aldol process. The control experiments and theoretical density functional theory investigation revealed that the reversible NaOAc-facilitated aza-aldol process led to the diastereomeric conversion to provide a stable product.

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An Easy Access to the Synthesis of Sugar‐Based N‐Methyl‐Pyrrolidine via [3 + 2] Cycloaddition Methodology

Cited by 4 publications

References 38 publications

ChemInform Abstract: An Easy Access to the Synthesis of Sugar‐Based N‐Methyl‐Pyrrolidine via [3 + 2] Cycloaddition Methodology.

ChemInform Abstract: An Easy Access to the Synthesis of Sugar‐Based N‐Methyl‐Pyrrolidine via [3 + 2] Cycloaddition Methodology.

Recent update on the role of N-methyl glycine as a building block for the construction of N-heterocyclic frameworks

Enantioselective Formal [3 + 1 + 1] Cycloaddition Reaction by Ru(II)/Iminium Cocatalysis for Construction of Multisubstituted Pyrrolidines

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