The diastereoselective synthesis of boron and carbon
vicinal stereogenic
centers is a great challenge in current synthetic chemistry due to
the paucity of efficient synthetic strategies. Herein, a Cu-catalyzed
diastereo- and enantioselective B–H bond insertion reaction
of ene-yne-ketones as furyl-carbene precursors has been developed
using chiral bis(oxazolines) (BOX) as the ligand, thus furnishing
a series of densely functionalized products (42 examples) bearing
both boron and carbon vicinal stereogenic centers in high enantioselectivity
and high diastereoselectivity (up to 99% ee and > 20:1 dr) with
good
yields (up to 98%).
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