Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 19, Pages 5897-5900Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100143
Keywords
asymmetric catalysis; cyclization; isomerization; ketones; nickel
Categories
Funding
- Engineering and Physical Sciences Research Council
- AstraZeneca [EP/S513854/1]
- University of Nottingham
- GlaxoSmithKline
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This study describes a novel domino reaction involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization onto acyclic ketones to yield chiral tertiary-alcohol-containing products with high enantioselectivities. The reversible E/Z isomerization of the alkenylnickel intermediates allows overall anti-arylmetallative cyclization to occur, producing products with ring systems similar to certain diarylindolizidine alkaloids.
Domino reactions involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization of the alkenylnickel intermediates onto tethered acyclic ketones to give chiral tertiary-alcohol-containing products in high enantioselectivities, are described. The reversible E/Z isomerization of the alkenylnickel intermediates enables overall anti-arylmetallative cyclization to occur. The ring system of the products are substructures of certain diarylindolizidine alkaloids.
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