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Enantioselective 1,2-Carboamination of 1,3-Dienes with <i>N</i>-Hydroxyphthalimide (NHP) Esters Enabled by a Photoinduced Pd Catalysis

Zhilin Liu, Jia-Le Yan, Kai Chen, Hao‐Yue Xiang, Hua Yang

2024Organic Letters17 citationsDOI

Abstract

Herein, a photoinduced, Pd-catalyzed direct 1,2-carboamination of conjugated 1,3-dienes has been successfully achieved. Sequential regioselective C–C bond and enantioselective C–N bond formation allows rapid assembly of a wide range of value-added chiral allylic amines from readily available N -hydroxyphthalimide (NHP) esters and 1,3-dienes under mild conditions. This developed protocol further demonstrates the versatility and potency of the photoexcited Pd catalytic system with a bifunctional reagent in the streamlined difunctionalization of C═C bonds.

Topics & Concepts

ChemistryEnantioselective synthesisCatalysisCombinatorial chemistryOrganic chemistryOptically activeMedicinal chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry
Enantioselective 1,2-Carboamination of 1,3-Dienes with <i>N</i>-Hydroxyphthalimide (NHP) Esters Enabled by a Photoinduced Pd Catalysis | Litcius