Copper-Catalyzed Enantioselective Hydroboration of Unactivated 1,1-Disubstituted Alkenes

We report an efficient and highly enantioselective hydroboration of aliphatic 1,1-disubstituted alkenes with pinacolborane using a phosphine-Cu catalyst. The method allows facile preparation of enantiomerically enriched β-chiral alkyl pinacolboronates from a range of 1,1-disubstituted alkenes with h...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-10, Vol.139 (39), p.13660-13663
Main Authors: Jang, Won Jun, Song, Seung Min, Moon, Jong Hun, Lee, Jin Yong, Yun, Jaesook
Format: Article
Language:English
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Summary:We report an efficient and highly enantioselective hydroboration of aliphatic 1,1-disubstituted alkenes with pinacolborane using a phosphine-Cu catalyst. The method allows facile preparation of enantiomerically enriched β-chiral alkyl pinacolboronates from a range of 1,1-disubstituted alkenes with high enantioselectivity up to 99% ee. Unprecedented enantiodiscrimination between the geminal alkyl substituents was observed with functional group compatibility in the hydroboration. Furthermore, a catalyst loading as low as 1 mol % furnished the desired product without a decrease in yield or selectivity, demonstrating its efficiency in gram scale synthesis.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b08379