Copper-catalyzed enantioselective hydroboration of unactivated 1, 1-disubstituted alkenes

Won Jun Jang, Seung Min Song, Jong Hun Moon, Jin Yong Lee, Jaesook Yun

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103 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)13660-13663
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number39
DOIs
StatePublished - 4 Oct 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

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