A new approach has been developed for the synthesis of N-alkylpyrroles with a chiral substituent at the nitrogen atom by the Paal-Knorr reaction using esters of amino acids as the source of chirality.
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Notes
Here and subsequently, there was no determination of the absolute configuration for compounds 1 and 4. The indicated S-configuration for compounds1 and 4 was assigned on the basis of the S-configuration of the starting amino acid esters since the chiral site in the key transformation is not affected.
The IR and mass spectra taken for the optically active pyrroles were identical to the spectra of the corresponding racemic samples.
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Dedicated to L. I. Belen'kii on the occasion of his eightieth birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 231–244, February, 2011.
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Ryzhkov, I.O., Andreev, I.A., Belov, G.M. et al. Preparation of chiral pyrrole derivatives by the Paal-Knorr reaction. Chem Heterocycl Comp 47, 182–193 (2011). https://doi.org/10.1007/s10593-011-0739-7
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DOI: https://doi.org/10.1007/s10593-011-0739-7