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Synlett 2015; 26(13): 1831-1834
DOI: 10.1055/s-0034-1380428
DOI: 10.1055/s-0034-1380428
letter
Manganese(II)-Catalyzed Esterification of N-β-Hydroxyethylamides
Weitere Informationen
Publikationsverlauf
Received: 29. April 2015
Accepted after revision: 18. Mai 2015
Publikationsdatum:
26. Juni 2015 (online)
Abstract
A catalyst system of manganese with 2,2-bipyridine for amide alcoholysis of N-β-hydroxyethylamides is described. This protocol enabled selective cleavage of the amide bond through a mechanism involving sequential N,O-acyl rearrangement and transesterification.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380428.
- Supporting Information
-
References and Notes
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- 16 Procedure of a Crossover Experiment (Scheme 2) An oven-dried Schlenk tube was equipped with Mn(acac)2 (0.05 mmol), N-(2-hydroxyethyl)benzamide (1d) (1.0 mmol), N-hexyl-3-phenylpropionamide (4, 1.0 mmol), 2,2′-bipyridine (0.05 mmol), diethyl carbonate (2.0 mmol), and n-BuOH (1.0 mL), and the resulting mixture was refluxed for 18 h under an argon atmosphere. After cooling to r.t., metal salts were removed by filtration through silica gel eluting with EtOAc, and solvents were removed in vacuo. Yield and conversion were determined by 1H NMR analysis using phenanthrene as an internal standard.
For recent reviews, see:
For recent reviews, see:
For examples using activated acyl compounds, see:
For directing-group-assisted reactions, see:
For reactions of twisted amides, see:
For examples on the catalytic esterification, see:
For examples of the oxazolidone auxiliary alcoholysis, see: