Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 22, Pages 5775-5778Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801070
Keywords
asymmetric catalysis; boron; chiral amine; copper; electrophilic amination
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Funding
- JSPS KAKENHI [JP 15H05485, JP 17H06092]
- Grants-in-Aid for Scientific Research [17H06092] Funding Source: KAKEN
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A CuCl/(R,R)-PTBP-BDPP-catalyzed regioselective and enantioselective aminoboration of simple and unactivated terminal alkenes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. The amino group and boryl group were incorporated at the internal position and terminal position, respectively, and the corresponding chiral beta-borylalkylamines were obtained with good to high enantiomeric ratios. The asymmetric copper catalysis allows rapid and concise transformation of readily available olefinic feedstock-like materials into functionalized chiral alkylamines of high potential in medicinal and pharmaceutical chemistry.
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