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

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.

journal_name

Nat Commun

journal_title

Nature communications

authors

Chen Y,Dang L,Ho CY

doi

10.1038/s41467-020-16139-2

subject

Has Abstract

pub_date

2020-05-08 00:00:00

pages

2269

issue

1

issn

2041-1723

pii

10.1038/s41467-020-16139-2

journal_volume

11

pub_type

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