Journal
ORGANIC LETTERS
Volume 16, Issue 17, Pages 4658-4661Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5022417
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Funding
- NSF [CHE-136273]
- NIH [GM-47480]
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Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0-5.0 mol % of chiral NHC-Cu complexes, B-2(pin)(2), and t-BuOH proceed to afford allcenyl-B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What's more, the corresponding boronic acids may be used in highly stereoselective NHC-Cu-catalyzed allylic substitution reactions.
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