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Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides

Ruihua Liu, Zhen‐Yao Shen, Cong Wang, Teck‐Peng Loh, Xu‐Hong Hu

2020Organic Letters32 citationsDOI

Abstract

We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C–H acylation of enamide rather than at N–H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.

Topics & Concepts

ChemistryAcylationCombinatorial chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis