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Copper-Catalyzed Enantioselective Hydroboration of Unactivated 1,1-Disubstituted Alkenes
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2017-09-18 00:00:00 , DOI: 10.1021/jacs.7b08379
Won Jun Jang 1 , Seung Min Song 1 , Jong Hun Moon 1 , Jin Yong Lee 1 , Jaesook Yun 1
Affiliation  

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.

中文翻译:

铜催化未活化的1,1-二取代烯烃的对映选择性硼氢化

我们报告了使用膦-Cu催化剂与频哪醇硼烷对脂肪族1,1-二取代烯烃进行高效且高度对映选择性的硼氢化反应。该方法使得可以容易地制备对映体富集的β-手性烷基频哪醇硼酸酯,所述β-手性烷基频哪醇硼酸酯具有高达99%ee的高对映选择性的范围的1,1-二取代的烯烃。在硼氢化中具有官能团相容性的情况下,观察到双子烷基取代基之间前所未有的对映异构。此外,低至1mol%的催化剂负载量提供了所需产物,而收率或选择性没有降低,证明了其在克规模合成中的效率。
更新日期:2017-09-19
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