info:eu-repo/semantics/article
Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture
Fecha
2019-01Registro en:
Cankarova, Nadezda; la Venia, Agustina; Krajcovicova, Sona; Krchnak, Viktor; Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture; American Chemical Society; Journal of Organic Chemistry; 84; 2; 1-2019; 636-644
0022-3263
CONICET Digital
CONICET
Autor
Cankarova, Nadezda
la Venia, Agustina
Krajcovicova, Sona
Krchnak, Viktor
Resumen
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.