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Synthesis and structure of diastereomeric trans-3,4-diamino-2,2,6,6-tetramethylpiperidine1-oxyl derivatives

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The reaction of 3,4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl with (1S)-(+)-camphor-10-sulfonyl chloride gives a mixture of diastereomeric 4-monosulfonylamino derivatives. The products of their acylation have been obtained. The 3,4-bis-[(1S)-camphor-10-sulfonylamino] derivative was synthesized and resolved to individual diastereomers. For one of them thetrans relationship of the 3- and 4-substituents and the absolute (3S,4R)-configuration were established by X-ray structural analysis.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 367–372, February, 1993.

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Sen', V.D., Tkachev, V.V. & Atovmyan, L.O. Synthesis and structure of diastereomeric trans-3,4-diamino-2,2,6,6-tetramethylpiperidine1-oxyl derivatives. Russ Chem Bull 42, 328–333 (1993). https://doi.org/10.1007/BF00697088

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Key words

  • trans-3.4-diamino-2,2,6,6-tetramethylpiperidine-1-oxyl
  • diastereomeric derivatives, resolution
  • structure
  • absolute configuration