Conformational analysis of N-Boc-N,O-isopropylidene-alpha-serinals. A Combined DFT and NMR study

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Corzana, F. 1
  4. Jiménez-Osés, G. 1
  5. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Año de publicación: 2003

Volumen: 59

Número: 30

Páginas: 5713-5718

Tipo: Artículo

DOI: 10.1016/S0040-4020(03)00852-4 SCOPUS: 2-s2.0-0037630621 WoS: WOS:000184306000010 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

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.