Oana Moldovan, Iulia Nagy, P. Lameiras
Jul 31, 2015
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Starting from commercial C-2-substituted 2-aminopropane-1,3-diols ( serinols , ‘ open-chain ’ peripheral units) and optically active amino-1,3-dioxanes (‘ closed-chain ’ peripheral units) as cycloacetals of (1 S ,2 S )-2-amino-1-(4-nitrophenyl)propane-1,3-diol ( p-nitrophenylserinol ) or its 2-dimethylamino analogue, we herein report a new series of di- and trimeric G-1 trispiro-dendritic melamines, they were synthesised convergently by iterative chemoselective amination of cyanuric chloride. Depending on the number of hydroxymethyl groups in the ‘ open-chain ’ peripheral unit and the type of the rigid amino-anchorage (axial or equatorial) of the ‘ closed-chain ’ counterpart, the classic restricted rotation about the C( s -triazine)–N(exocyclic) partial double bonds induced, progressively, specific spatial arrangements in angularly connected G-0 and G-1 dendrons, including axial chirality in G-1 dimeric or G-1 trimeric melamines.