Asymmetric Semipinacol Rearrangement Enabled by Copper-Catalyzed Propargylic Alkylation
Fan Gong, Xiangjian Meng, Shouang Lan, Jinggong Liu, Shuang Yang, Xinqiang Fang
Abstract
The merger of two powerful synthetic strategies, i.e., asymmetric semipinacol-type rearrangement and transition-metal-catalyzed propargylic alkylation, has been achieved, delivering a range of enantioenriched cyclo- and heterocyclopentanones with α-alkynylated quaternary stereocenters. Such types of products are challenging to obtain using other methods, and their synthetic value has been demonstrated in a variety of further transformations. The work represents a distinctive mode inducing asymmetric 1,2-carbon migration and further expands the scope of propargylic substitution.
Topics & Concepts
StereocenterAlkylationCombinatorial chemistryCatalysisEnantioselective synthesisChemistryCopperOrganic chemistryCatalytic Alkyne ReactionsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods