Journal
TETRAHEDRON LETTERS
Volume 59, Issue 21, Pages 2030-2033Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.04.030
Keywords
5-NT2C agonists; Asymmetric synthesis; Lorcaserin; Sulfamidate; Tetrahydronaphthyridines
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Asymmetric syntheses of N-protected (R)-4-halo-6,6a,7,8,9,10-hexahydro-5H-pyrazino[1,2-a][1,n]naphthyridines, advanced intermediates for the synthesis of highly potent and selective 5-HT2C agonists, are described. The key transformation involves ring opening of N-protected bicyclic sulfamidate (R)hexahydro-3H-pyrazino[1,2-c][1,2,3]oxathiazine 1,1-dioxide with (4-halo-2-fluoropyridin-3-yl)lithiums or (3-bromo-5-fluoropyridin-4-yl)lithium. In situ hydrolyses of the resultant sulfamic acids and subsequent intramolecular nucleophilic aromatic substitutions (SNAr) produce the enantiopure tricycles. The two step procedure represents new methodology for the stereoselective syntheses of tetrahydronaphthyridines. (C) 2018 Elsevier Ltd. All rights reserved.
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