Highly Atroposelective Rhodium(II)-Catalyzed N–H Bond Insertion: Access to Axially Chiral N-Arylindolocarbazoles,ACS Catalysis

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Highly Atroposelective Rhodium(II)-Catalyzed N–H Bond Insertion: Access to Axially Chiral N-Arylindolocarbazoles
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-05-06 , DOI: 10.1021/acscatal.1c01232
Qiao Ren _{1,

2} , Tingting Cao ₁ , Chunnian He ₁ , Meihua Yang ₁ , Haitao Liu ₁ , Lei Wang ₁

Affiliation

The highly atroposelective construction of axially chiral N-arylindolocarbazoles is disclosed via the Rh(II)-catalyzed intermolecular carbene N–H insertion reactions. This straightforward transformation provides a rapid access to a wide range of enantio-enriched N-arylindolocarbazole atropisomers bearing the C–N axis in moderate to good yields and high enantioselectivities. Also, the synthetic utility of this protocol is unambiguously emphasized by the late-stage functionalization (LSF) of some representative natural products and bioactive molecules. Furthermore, the polyaromatic ring construction and N-arylindolocarbazole-derived chiral phosphoric acid (CPA) synthesis also highlight its practical value in materials chemistry and catalytic asymmetric synthesis.

中文翻译：

高度对映选择性的铑（II）催化的NH键插入：获得轴向手性N-芳基吲哚并咔唑

通过Rh（II）催化的分子间卡宾NH插入反应公开了轴向手性N-芳基吲哚并咔唑的高度对映选择性。这种简单的转化可以快速获得各种带有C–N轴的对映体富集的N-芳基吲哚并咔唑阻转异构体，且产率中等至良好，对映选择性很高。同样，某些代表性天然产物和生物活性分子的后期功能化（LSF）明确强调了该协议的合成效用。此外，聚芳环的结构和N芳基吲哚并咔唑衍生的手性磷酸（CPA）合成也突出了其在材料化学和催化不对称合成中的实用价值。

更新日期：2021-05-22

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