Conformational analysis of N-Boc-N,O-isopropylidene-alpha-serinals. A Combined DFT and NMR study
This work describes an extensive conformational analysis of Garner's aldehyde and its α-methylated homologue - two important chiral building blocks that are widely used in organic synthesis. A combination of density-functional theory and NMR spectroscopy confirmed the existence of a dynamic equ...
| Autores: | , , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2003 |
| País: | España |
| Recursos: | Universidad de La Rioja (UR) |
| Repositório: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc690bb750603269e81411 |
| Acesso em linha: | https://investigacion.unirioja.es/documentos/5bbc690bb750603269e81411 |
| Access Level: | Acceso aberto |
| Palavra-chave: | Density-functional theory Dipole moment Garner's aldehyde |
| Resumo: | This work describes an extensive conformational analysis of Garner's aldehyde and its α-methylated homologue - two important chiral building blocks that are widely used in organic synthesis. A combination of density-functional theory and NMR spectroscopy confirmed the existence of a dynamic equilibrium between two possible conformers of the carbamate group in these compounds. The calculated properties such as conformer populations and rotational barriers around the (C=O)-N bond are in good agreement with the experimental values. Finally, the dipole moments of the molecules appear to be a decisive factor in the stabilization of the conformers in solution. © 2003 Elsevier Ltd. All rights reserved. |
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