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Asymmetric nitrogen

79. Transfer of chirality from nitrogen to carbon in transformations of dimethyl 1-methoxyaziridine-2,2-dicarboxylate and synthesis of dimethyl 1-silyloxyaziridine-2,2-dicarboxylate

  • Organic Chemistry
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Abstract

The possibility of tranferring chirality from nitrogen to carbon by a three-step transformation of racemic dimethyl 1-methoxyaziridine-2,2-dicarboxylate into 3-amino-2-chloromethyl-2-methoxyaminopropan-1-ol was demonstrated. The first representative of 1-silyloxyaziridines,viz., dimethyl 1-(tert-butyldimethylsilyloxy)aziridine-2,2-dicarboxylate, was synthesized by acidolysis or thermolysis of triazoline, obtained by the reaction oftert-butyldimethylsilyloxime of dimethy mesoxalate with CH2N2

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Authors and Affiliations

  1. Ukrainian State University of Chemistry and Technology, 6 pros. Gagarina, 32005, Dnepropetrovsk, Ukraine

    V. V. Rozhkov

  2. N. N. Semenov Institute of Chemical Physics, Russian academy of Sciences, 4 ul. Kosygina, 117977, Moscow, Russian Federation

    V. N. Voznesenskii & R. G. Kostyanovsky

Authors
  1. V. V. Rozhkov
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  2. V. N. Voznesenskii
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  3. R. G. Kostyanovsky
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Additional information

For Part 78, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 116–119, January, 1998.

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Rozhkov, V.V., Voznesenskii, V.N. & Kostyanovsky, R.G. Asymmetric nitrogen. Russ Chem Bull 47, 115–118 (1998). https://doi.org/10.1007/BF02495517

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  • DOI: https://doi.org/10.1007/BF02495517

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