期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 3, 页码 1490-1493出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja211269w
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资金
- NIH [GM-47480]
- NSF [CHE-1111074]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1111074] Funding Source: National Science Foundation
Catalytic enantioselective allylic substitutions that result in addition of an allenyl group (<2% propargyl addition) and formation of tertiary or quaternary C-C bonds are described. Commercially available allenylboronic acid pinacol ester is used. Reactions are promoted by a 5.0-10 mol % loading of sulfonate-bearing chiral bidentate N-heterocyclic carbene (NHC) complexes of copper, which exhibit the unique ability to furnish chiral products arising from the S(N)2' mode of addition. Allenyl-containing products are generated in up to 95% yield, >98% S(N)2 selectivity, and 99:1 enantiomeric ratio (er). Site-selective NHC-Cu-catalyzed hydroboration of enantiomerically enriched allenes and conversion to the corresponding beta-vinyl ketones demonstrates the method's utility.
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