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Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution

Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl... ISSN 0012-5008, Doklady Chemistry, 2018, Vol. 483, Part 2, pp. 293–296. © Pleiades Publishing, Ltd., 2018. Original Russian Text © D.A. Gruzdev, E.N. Chulakov, L.Sh. Sadretdinova, G.L. Levit, V.P. Krasnov, V.N. Charushin, 2018, published in Doklady Akademii Nauk, 2018, Vol. 483, No. 4. CHEMISTRY Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution a,b a a a,b, D. A. Gruzdev , E. N. Chulakov , L. Sh. Sadretdinova , G. L. Levit *, a,b, a,b V. P. Krasnov **, and Academician V. N. Charushin Received July 18, 2018 Abstract—The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 3,4-dihy- dro-3-methyl-2H-[1,4]benzoxazines with acyl chlorides of N-naphthaloyl-(S)-alanine and N-naphthaloyl- (S)-phenylalanine has been studied. It has been shown that diastereoselective acylation of racemic amines with N-naphthaloyl (S)-amino acyl chlorides results in the predominant formation of (R,S)-amides, whereas acylation of the same amines with N-phthaloyl (S)-amino acyl chlorides proceeds with the opposite diaste- reoselectivity. The parallel kinetic resolution of racemic 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using a mixture of acylating agents derived from a single precursor, (S)-phenylalanine, was carried out. DOI: 10.1134/S0012500818120017 In the arsenal of modern medicinal agents, the [2, 9], and 2-aryloxypropionic acids [11, 12] are con- enantiomerically http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Doklady Chemistry Springer Journals

Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution

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References (13)

Publisher
Springer Journals
Copyright
Copyright © 2018 by Pleiades Publishing, Inc.
Subject
Chemistry; Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering
ISSN
0012-5008
eISSN
1608-3113
DOI
10.1134/S0012500818120017
Publisher site
See Article on Publisher Site

Abstract

ISSN 0012-5008, Doklady Chemistry, 2018, Vol. 483, Part 2, pp. 293–296. © Pleiades Publishing, Ltd., 2018. Original Russian Text © D.A. Gruzdev, E.N. Chulakov, L.Sh. Sadretdinova, G.L. Levit, V.P. Krasnov, V.N. Charushin, 2018, published in Doklady Akademii Nauk, 2018, Vol. 483, No. 4. CHEMISTRY Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution a,b a a a,b, D. A. Gruzdev , E. N. Chulakov , L. Sh. Sadretdinova , G. L. Levit *, a,b, a,b V. P. Krasnov **, and Academician V. N. Charushin Received July 18, 2018 Abstract—The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 3,4-dihy- dro-3-methyl-2H-[1,4]benzoxazines with acyl chlorides of N-naphthaloyl-(S)-alanine and N-naphthaloyl- (S)-phenylalanine has been studied. It has been shown that diastereoselective acylation of racemic amines with N-naphthaloyl (S)-amino acyl chlorides results in the predominant formation of (R,S)-amides, whereas acylation of the same amines with N-phthaloyl (S)-amino acyl chlorides proceeds with the opposite diaste- reoselectivity. The parallel kinetic resolution of racemic 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using a mixture of acylating agents derived from a single precursor, (S)-phenylalanine, was carried out. DOI: 10.1134/S0012500818120017 In the arsenal of modern medicinal agents, the [2, 9], and 2-aryloxypropionic acids [11, 12] are con- enantiomerically

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Doklady Chemistry – Springer Journals

Published: Jan 16, 2019

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