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Enantioselective [3 + 2] Cycloaddition of Vinylcyclopropanes with Alkenyl <i>N</i>-Heteroarenes Enabled by Palladium Catalysis

Wen‐Dao Chu, Yating Wang, Tian-Tian Liang, Teng Long, Jia-Yu Zuo, Zhihui Shao, Bo Chen, Cheng‐Yu He, Quan‐Zhong Liu

2022Organic Letters18 citationsDOI

Abstract

The first catalytic enantioselective [3 + 2] cycloaddition reaction between vinylcyclopropanes and alkenyl N-heteroarenes in the presence of LiBr and a Pd(0)/SEGPHOS complex was developed. LiBr plays a key role in improving the reactivity of alkenyl N-heteroarenes as a mild Lewis acid.

Topics & Concepts

Enantioselective synthesisChemistryCycloadditionCatalysisReactivity (psychology)PalladiumLewis acids and basesOrganic chemistryCombinatorial chemistryMedicinal chemistryAlternative medicineMedicinePathologyCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods