Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
J Am Chem Soc. 2017 Oct 4;139(39):13660-13663. doi: 10.1021/jacs.7b08379. Epub 2017 Sep 18.
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.
我们报道了一种使用膦-Cu 催化剂高效、高对映选择性的频哪醇硼烷对脂肪族 1,1-二取代烯烃的硼氢化反应。该方法可从一系列 1,1-二取代烯烃中轻松制备对映体富集的β-手性烷基频哪醇硼酸盐，对映选择性高达 99%ee。在硼氢化反应中观察到了偕二烷基取代基之间前所未有的对映体选择性，同时具有官能团相容性。此外，在不降低产率或选择性的情况下，催化剂用量低至 1mol%即可得到所需产物，证明了其在克级合成中的效率。
