Abstract
Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species.
Highlights
T ransition-metal catalysis is utilized extensively in organic synthesis to prepare compounds required for numerous applications such as drug discovery, agrochemistry, and materials science
One strategy to obtain alkenylmetal species resulting from formal anti-carbometalation is to employ substrates with a heteroatom-containing substituent in close proximity to the alkyne
After syn-carbometalation, E/Z isomerization to the antiisomer is driven by the formation of a more stable, chelated alkenylmetal species, in which the metal is coordinated to the heteroatom.1b,2a,b,d,h effective, the requirement for a nearby heteroatom-containing group limits broader applicability
Summary
T ransition-metal catalysis is utilized extensively in organic synthesis to prepare compounds required for numerous applications such as drug discovery, agrochemistry, and materials science.
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