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Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine

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Abstract

Nucleophilic substitution of the halogen atom in dimethyl (S)-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2S,4S)-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2S,4S)-4-(indol-1-yl)-5-oxoproline; reduction of the carbonyl groups with BH3 yielded (2S,4S)-4-(indol-1-yl)prolines and (2S,4S)-2-hydroxymethyl-4-(indol-1-yl)pyrrolidines. Reduction of (2S,4S)-4-arylamino-5-oxoprolines with BH3 to the corresponding (2S,4S)-4-arylaminoprolines and (2S,4S)-4-arylamino-2-hydroxymethylpyrrolidines was studied.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620990, Ekaterinburg, Russian Federation

    A. Yu. Vigorov, I. A. Nizova, K. E. Shalunova, A. N. Grishakov, L. Sh. Sadretdinova, I. N. Ganebnykh, M. A. Ezhikova, M. I. Kodess & V. P. Krasnov

Authors
  1. A. Yu. Vigorov
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  2. I. A. Nizova
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  3. K. E. Shalunova
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  4. A. N. Grishakov
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  5. L. Sh. Sadretdinova
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  6. I. N. Ganebnykh
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  7. M. A. Ezhikova
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  8. M. I. Kodess
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  9. V. P. Krasnov
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Correspondence to V. P. Krasnov.

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Dedicated to Academician V. N. Charushin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 853–861, May, 2011.

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Vigorov, A.Y., Nizova, I.A., Shalunova, K.E. et al. Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine. Russ Chem Bull 60, 873–881 (2011). https://doi.org/10.1007/s11172-011-0137-4

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  • DOI: https://doi.org/10.1007/s11172-011-0137-4

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