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Synthesis of Nonracemic 9-(1-Methoxycarbonylethyl)-1,2,3,4-tetrahydrocarbazole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A new approach has been proposed to the synthesis of indole derivatives containing a chiral substituent at the nitrogen atom, comprizing Fischer indolization of phenylhydrazines with a chiral substituent at the α-nitrogen atom. The initial hydrazines were obtained by the alkylation (Mitsunobu reaction applying optically active esters of lactic acid) of anilines containing an electron-accepting substituent at the amino group. Subsequent removal of the activating acceptor grouping was realized by nitrosation of the chiral secondary aniline followed by reduction of the corresponding N-nitroso compound.

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Authors and Affiliations

  1. Moscow M. V. Lomonosov State University, Moscow, 119234, Russia

    A. V. Kurkin, V. V. Nesterov, A. V. Karchava & M. A. Yurovskaya

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  1. A. V. Kurkin
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  2. V. V. Nesterov
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  3. A. V. Karchava
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  4. M. A. Yurovskaya
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Kurkin, A.V., Nesterov, V.V., Karchava, A.V. et al. Synthesis of Nonracemic 9-(1-Methoxycarbonylethyl)-1,2,3,4-tetrahydrocarbazole. Chemistry of Heterocyclic Compounds 39, 1466–1477 (2003). https://doi.org/10.1023/B:COHC.0000014411.33252.d1

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  • DOI: https://doi.org/10.1023/B:COHC.0000014411.33252.d1

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