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Unnatural amino acids. 3. Aziridinyl ketones from esters and amides of aziridine-2-carboxylic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A series of N-substituted amides and esters of aziridine-2-carboxylic acids have been prepared and have been subjected to deprotonation with lithium diisopropylamide. The intermediate carbanions reacted more readily with the carbonyl groups of the substrates than with methyl iodide. So, in place of the expected amides or esters of methylaziridine-2-carboxylic acids, amides or esters of 2-aziridinylcarbonylaziridine-2-carboxylic acids were isolated.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV1006, Latvia

    B. Shtrumfs, J. Hermane, I. Kalvinsh & P. Trapencieris

Authors
  1. B. Shtrumfs
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  2. J. Hermane
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  3. I. Kalvinsh
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  4. P. Trapencieris
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, 220–225, February, 2007.

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Shtrumfs, B., Hermane, J., Kalvinsh, I. et al. Unnatural amino acids. 3. Aziridinyl ketones from esters and amides of aziridine-2-carboxylic acids. Chem Heterocycl Compd 43, 169–174 (2007). https://doi.org/10.1007/s10593-007-0028-7

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  • DOI: https://doi.org/10.1007/s10593-007-0028-7

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