Journal
TETRAHEDRON
Volume 63, Issue 44, Pages 10801-10808Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.05.129
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This paper describes our attempts to synthesize inherently chiral heteroatom-bridged calixaromatics. Based on a stepwise fragment-coupling approach using a chiral 3,5-dihydroxybenzamide or benzoate, 2,4-dihydroxyacetophenone, and cyanuric chloride as reactants, chiral tetraoxacalix[2]arene[2]triazine derivatives 16 and 17 were synthesized in good yields. Subsequent macrocyclic condensation with a diamine 6 furnished efficiently the pairs of diastereomers of inherently chiral tetraoxacalix[2]arene[2]triazine azacrowns 18 and 19. (C) 2007 Elsevier Ltd. All rights reserved.
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