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DOI: 10.1055/a-1990-4867
Diastereoselective Synthesis of Secondary Propargylamines Exploiting CuI-Based Promoters and Determination of Their Relative Configuration by DFT-GIAO Conformational Analysis
The work was financially supported by the University of Camerino under the framework of the University Research Project ‘FAR2018: Fondo di Ateneo per la Ricerca’. The authors are thankful to Fratelli Guzzini Recanati for granting a doctoral fellowship to M.L.
Abstract
The stereoselective synthesis of several secondary propargylamines by the copper-promoted A3-coupling reaction of aliphatic and aromatic aldehydes with phenylacetylene and (R)-(+)-phenylethylamine is here reported. Two different synthetic methodologies have been investigated in this study, involving CuSO4/NaI and CeCl3·7H2O/CuI promoting systems. The reported methodologies were compared in terms of efficiency, diastereoselectivity, and toxicity, both showing advantages with respect to the current methodologies. The relative configurations of each of the obtained propargylamines, previously unknown in the literature, were assigned by comparison of the 1H NMR experimental chemical shifts with those theoretically predicted via the DFT-GIAO method.
Key words
propargylamines - A3 coupling - relative configuration - copper promoter - DFT calculations - stereoselective synthesis - diastereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1990-4867. The computational data sets generated for this study are available upon reasonable request to the corresponding author.
- Supporting Information
Publication History
Received: 12 October 2022
Accepted after revision: 30 November 2022
Accepted Manuscript online:
30 November 2022
Article published online:
20 January 2023
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