Org Lett. 2018 Sep 21;20(18):5757-5761. doi: 10.1021/acs.orglett.8b02457. Epub 2018 Sep 10.
The design, synthesis, and evaluation of axial-chiral biisoquinolines bearing polar aromatic C-H bonds as Lewis base catalysts are reported. Lewis bases containing the 3,5-bis(trifluoromethyl)phenyl group were found to be significantly more enantioselective for a wider range of substrates than those bearing aromatic residues that are not strongly electron-deficient in the allylation of aldehydes with allyltrichlorosilane. Also, optically pure 3,3'-dibromo-1,1'-biisoquinoline N, N'-dioxide that has not been previously reported was synthesized as a common catalyst precursor to facilitate the study.
本文报道了具有轴向手性的双异喹啉，并对其进行了设计、合成和评价，这些双异喹啉含有极性芳香 C-H 键，可用作路易斯碱催化剂。与含有非强缺电子芳基的路易斯碱相比，含有 3,5-双（三氟甲基）苯基的路易斯碱在烯丙基三氯硅烷对醛的烯丙基化反应中，对更广泛的底物具有更高的对映选择性。此外，还合成了以前未曾报道过的旋光纯 3,3'-二溴-1,1'-双异喹啉 N, N'-二氧化物，用作常见的催化剂前体，以方便研究。
