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Copper-Catalyzed Enantioselective Hydroboration of Unactivated 1,1-Disubstituted Alkenes
Won Jun Jang1, Seung Min Song1, Jong Hun Moon1
1Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
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.
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