Stereoselective Aza-Henry Reaction of 3-Nitro-dihydro-2(1H)-quinolones with N-Boc-Aldimines under the Catalysis of Chiral Ammonium Betaines

Azacycles such as indoles and tetrahydroquinolines are privileged structures in drug development. Reported here is an unprecedented regiodivergent intramolecular nucleophilic addition reaction of imines as aflexible approach to access Nfunctionalizedindoles and tetrahydroquinolines,bythe control of reaction at the N-terminus and C-terminus,r espectively. Using ketimines derived from 2-(2-nitroethyl)anilines with isatins or a-ketoesters,t he regioselective N-attackr eaction gives N-functionalized indoles,w hile the catalytic enantioselective C-attackr eaction affords chiral tetrahydroquinolines featuring an a-tetrasubstituted stereocenter.M echanistic studies reveal that hydrogen-bonding interactions may greatly facilitate such unusual N-attackreactions of imines.The utility of this protocol is highlighted by the catalytic enantioselective formal synthesis of (À)-psychotrimine,and the construction of various fused aza-heterocycles. Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.1002/anie.201910864. Angewandte Chemie Research Articles Scheme 1. Reaction design and development. M.S. = moleculars ieves, Ts = 4-toluenesulfonyl.Figure 8. Synthetic applicationsofN-functionalized indole derivatives. X-ray structure for 21 shown. [36] AIBN = 2,2'-azobis(isobutyronitrile), LAH = lithium aluminumhydride, Ns = 4-nitrobenzenesulfonyl, TEA = triethylamine.

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Regiodivergent Intramolecular Nucleophilic Addition of Ketimines for the Diverse Synthesis of Azacycles

Wang

Tian

Tan

et al. 2019

Angewandte Chemie

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Regiodivergent Intramolecular Nucleophilic Addition of Ketimines for the Diverse Synthesis of Azacycles

et al. 2019

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Progress in the Chemistry of Tetrahydroquinolines

2019

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Stereoselective Aza-Henry Reaction of 3-Nitro-dihydro-2(1H)-quinolones with N-Boc-Aldimines under the Catalysis of Chiral Ammonium Betaines

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Regiodivergent Intramolecular Nucleophilic Addition of Ketimines for the Diverse Synthesis of Azacycles

Regiodivergent Intramolecular Nucleophilic Addition of Ketimines for the Diverse Synthesis of Azacycles

Regiodivergent Intramolecular Nucleophilic Addition of Ketimines for the Diverse Synthesis of Azacycles

Progress in the Chemistry of Tetrahydroquinolines

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