School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou 221116 , P. R. China.
Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences , Nanjing University , Nanjing 210093 , P. R. China.
Org Lett. 2018 Nov 2;20(21):6616-6621. doi: 10.1021/acs.orglett.8b02374. Epub 2018 Sep 14.
A new class of chiral N-sulfonyl bisimidazoline (Bim) ligands have been designed, prepared, and applied in Pd(II)-catalyzed asymmetric addition of arylboronic acids to isatin-derived N-Boc ketimines. The combination of Pd(OCOCF) and N-tosyl Bim ligand shows high catalytic activity and excellent asymmetric induction, enabling asymmetric addition to offer α-tertiary amines with generally good to high yields and excellent enantioselectivity (up to 96% yield, 96% ee). This asymmetric Pd(II) catalysis can tolerate air conditions, providing a practical and operationally simple protocol toward the construction of an enantioenriched α-tertiary stereocenter.
一类新型的手性 N-磺酰基双咪唑啉（Bim）配体已经被设计、制备并应用于钯（II）催化的芳基硼酸对吲哚啉衍生的 N-Boc 亚胺的不对称加成反应中。Pd(OCOCF₃)₂和 N-对甲苯磺酰基 Bim 配体的组合显示出高的催化活性和优异的对映选择性，使得不对称加成反应能够以一般良好到高的收率和优异的对映选择性（高达 96%的产率，96%ee）提供α-叔胺产物。这种不对称的钯（II）催化反应可以耐受空气条件，为构建对映富集的α-叔立体中心提供了一种实用且操作简单的方法。
