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Comparative study of the different approaches to the synthesis of isatins with a chiral substituent at the nitrogen atom

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Chemistry of Heterocyclic Compounds Aims and scope

Through a comparative study of three different routes to the synthesis of isatins with a chiral substituent on the nitrogen atom it has been shown that better results for preparing the isatins are achieved using the Sandmeyer (>99% ee, yield 50%) rather than the Stolle method (95% ee, yield 16%). The procedure proposed by Gassman for preparing isatins was unsuitable for the compounds described.

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Authors and Affiliations

  1. M. V. Lomonosov State University, Moscow, 119991, Russia

    A. V. Kurkin, A. A. Bernovskaya & M. A. Yurovskaya

Authors
  1. A. V. Kurkin
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  2. A. A. Bernovskaya
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  3. M. A. Yurovskaya
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Correspondence to A. V. Kurkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1497-1504, October, 2010.

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Kurkin, A.V., Bernovskaya, A.A. & Yurovskaya, M.A. Comparative study of the different approaches to the synthesis of isatins with a chiral substituent at the nitrogen atom. Chem Heterocycl Comp 46, 1208–1214 (2011). https://doi.org/10.1007/s10593-011-0654-y

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  • DOI: https://doi.org/10.1007/s10593-011-0654-y

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