Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California , Berkeley, California 94720, United States.
J Am Chem Soc. 2016 Jun 1;138(21):6703-6. doi: 10.1021/jacs.6b02478. Epub 2016 May 20.
We report a two-step strategy for diverse hydrofunctionalizations of aliphatic internal alkenes with high regioselectivity and enantioselectivity. This process comprises a copper-catalyzed asymmetric hydroboration and subsequent stereospecific derivatizations of the secondary boronates. By this strategy, a range of compounds, such as amides, alkyl fluorides and bromides, alcohols, aldehydes, arenes, and heteroarenes, were synthesized from an internal alkene with high regioselectivity and enantioselectivity. Computational studies provide insight into the origins of these selectivities.
我们报告了一种两步策略，用于高区域选择性和对映选择性地对脂肪族内部烯烃进行多样化的氢官能化。该过程包括铜催化的不对称硼氢化反应和随后的仲硼酸酯的立体特异性衍生化。通过这种策略，可以从内部烯烃高区域选择性和对映选择性地合成各种化合物，如酰胺、烷基氟化物和溴化物、醇、醛、芳烃和杂芳烃。计算研究提供了对这些选择性起源的深入了解。
