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Enantioenriched 1,4-dienes are versatile building blocks in asymmetric synthesis, therefore their efficient synthesis directly from chemical feedstock is highly sought after. Here, we show an enantioselective cross-hydroalkenylation of cyclic 1,3-diene and hetero-substituted terminal olefin by using a chiral [NHC-Ni(allyl)]BAr F  catalyst. Using a structurally flexible chiral C 2  NHC-Ni design is key to access a broad scope of chiral 1,4-diene  3  or  3′  with high enantioselectivity. This study also offers insights on how to regulate chiral C 2  NHC-Ni(II) 1,3-allylic shift on cyclic diene  1  and to build sterically more hindered endocyclic chiral allylic structures on demand.

NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins