Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 22, Pages 9925-9931Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c03900
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Funding
- United States National Institutes of Health, Institute of General Medical Sciences [R01GM116987]
- National Science Foundation [CHE1726291]
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A method for the site-selective and diastereoselective conjugate addition of boron-stabilized allylic nucleophiles to alpha,beta-unsaturated ketones is disclosed. Transformations involve easily prepared gamma,gamma-disubstituted allyldiboron reagents and proceed in the presence of a fluoride activator at 80 degrees C. Reactions proceed with a wide variety of enones and allyldiboron reagents efficiently to deliver ketone products that contain otherwise difficult-to-access vicinal beta-tertiary and gamma-quaternary carbon stereogenic centers and an alkenylboron moiety. The utility of the method is highlighted by several transformations, including cross-coupling and carbocyclizations.
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