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

Yang Chen, Liang Dang () and Chun-Yu Ho ()
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Yang Chen: Southern University of Science and Technology (SUSTech)
Liang Dang: Southern University of Science and Technology (SUSTech)
Chun-Yu Ho: Southern University of Science and Technology (SUSTech)

Nature Communications, 2020, vol. 11, issue 1, 1-6

Abstract: Abstract 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)]BArF catalyst. Using a structurally flexible chiral C2 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 C2 NHC-Ni(II) 1,3-allylic shift on cyclic diene 1 and to build sterically more hindered endocyclic chiral allylic structures on demand.

Date: 2020
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DOI: 10.1038/s41467-020-16139-2

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