In:
Synthesis, Georg Thieme Verlag KG, Vol. 55, No. 08 ( 2023-04), p. 1241-1252
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.
Type of Medium:
Online Resource
ISSN:
0039-7881
,
1437-210X
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2023
detail.hit.zdb_id:
204080-3
detail.hit.zdb_id:
2033062-5
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