Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture

• Autores: Cankarova, Nadezda; la Venia, Agustina; Krajcovicova, Sona; Krchnak, Viktor
• Año de publicación: 2019
• Idioma: inglés
• Tipo de recurso: artículo
• Materia: 3D ARCHITECTURE; ABSOLUTE CONFIGURATION; HETEROCYCLES; MEDIUM-SIZED RINGS; MOLECULAR SCAFFOLD; SOLID-PHASE SYNTHESIS
• Institución: Consejo Nacional de Investigaciones Científicas y Técnicas

This report describes a configuration-dependent [6 + 8 + 5] fused ring formation via a tandem cyclic N-acyliminium nucleophilic addition reaction. Cyclization of the acyclic precursor prepared on a solid phase using l-Ser and a racemic mixture of Fmoc-trans-2-aminocyclohexanecarboxylic acid predominantly yielded the cyclic diastereomer with the (1R,2R)-2-aminocyclohexane moiety rather than the tricyclic diastereomer from the (1S,2S)-enantiomer. In contrast, the model compound prepared with d-Ser predominantly cyclized with the (1S,2S)-2-aminocyclohexanecarboxylic acid substrate. The outcome of the cyclization was not influenced by the type of resin, the spacer, or the N-substituent. The analogous synthesis of the [6 + 7 + 5] fused ring system yielded inseparable diastereomers in a 1:0.6 ratio.
Fil: Cankarova, Nadezda. Palacky University; República Checa
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Krajcovicova, Sona. Palacky University; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa