手性酸催化的非对映选择性吲哚化反应可用于构建具有手性 N-N 轴的 1,1'-吲哚-吡咯和双吲哚。
Chiral Acid-Catalyzed Atroposelective Indolization Enables Access to 1,1'-Indole-Pyrroles and Bisindoles Bearing a Chiral N-N Axis.
机构信息
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, China.
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore.
出版信息
Org Lett. 2023 Mar 10;25(9):1553-1557. doi: 10.1021/acs.orglett.3c00237. Epub 2023 Mar 1.
We present herein a highly atroposelective indolization for the efficient synthesis of 1,1'-biheteroaryls bearing a chiral N-N axis. Under the cooperative catalysis of chiral phosphoric acid and InBr, the reactions between 2,3-diketoesters and 1,3-dione-derived enamines resulted in a highly enantioselective construction of 1,1'-pyrrole-indoles with up to 92% yield, 94% enantiomeric excess (ee), or bisindoles in up to 92% ee. Derivatizations of these compounds to diverse functionalized N-N linked axially chiral biheteroaryls have also been demonstrated.
我们在此展示了一种高度对映选择性的吲哚化反应，用于高效合成具有手性 N-N 轴的 1,1'-双杂芳基。在手性磷酸和 InBr 的协同催化下，2,3-二酮酯和 1,3-二酮衍生的烯胺之间的反应以高对映选择性构建了 1,1'-吡咯-吲哚，产率高达 92%，对映体过量（ee）高达 94%，或双吲哚的 ee 高达 92%。还证明了这些化合物可以通过衍生化得到多种功能化的 N-N 连接的轴向手性双杂芳基。
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