A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism

An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the...

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Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (3), p.1040-1045
Main Authors: R. S, Reyno, Sugunan, Akash, S, Ranganayakulu, Suresh, Cherumuttathu H, Rajendar, Goreti
Format: Article
Language:English
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Summary:An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the former proceeds through the formation of an imine, the latter passes through the Michael addition–elimination mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04531