Conformational analysis of N-Boc-N,O-isopropylidene-alpha-serinals. A Combined DFT and NMR study
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Universidad de La Rioja
info
ISSN: 0040-4020
Year of publication: 2003
Volume: 59
Issue: 30
Pages: 5713-5718
Type: Article
More publications in: Tetrahedron
Abstract
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.