Efficient syntheses of new chiral peptidomimetic macrocycles through a configurationally driven preorganization |
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Authors: | Miriam Bru |
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Affiliation: | Departamento de Química Inorgánica y Orgánica, UAMOA, Universidad Jaume I/CSIC, Campus del Riu Sec, Avenida Sos Bainat, s/n, E-12071 Castellón, Spain |
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Abstract: | A new family of 32-membered ring peptidomimetic macrocycles has been efficiently obtained in a simple one-pot two-step reductive amination reaction, from easily prepared precursors. The structural and stereochemical variables have been explored in order to rationalize the obtained selectivity. The formation of the [2A+2B] tetraimine intermediate has been explained in terms of a very favorable configurationally driven preorganization as detected by NMR, CD and molecular modeling. |
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Keywords: | Preorganization Macrocycles Peptidomimetics Chiral receptors Supramolecular chemistry |
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