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. 2014 Jun 6;16(11):3158-61.
doi: 10.1021/ol501365j. Epub 2014 May 23.

The redox-Mannich reaction

Weijie Chen  1 , Daniel Seidel
Affiliations

The redox-Mannich reaction

Weijie Chen et al. Org Lett. .

Abstract

A complement to the classic three-component Mannich reaction, the redox-Mannich reaction, utilizes the same starting materials but incorporates an isomerization step that enables the facile preparation of ring-substituted β-amino ketones. Reactions occur under relatively mild conditions and are facilitated by benzoic acid.

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Figures

Scheme 1
Scheme 1. Scope of the Redox-Mannich Reaction with Pyrrolidine
Reactions were performed on a 0.5 mmol scale. A mixture of aldehyde and ketone in 0.5 mL of toluene was added over 5 h to a solution of pyrrolidine and benzoic acid in 2 mL of toluene. All yields correspond to isolated yields.
Scheme 2
Scheme 2. Scope of the Redox-Mannich Reaction with Tetrahydroisoquinoline
Reactions were performed on a 0.5 mmol scale. The substrates were mixed directly. All yields correspond to isolated yields. b 3 equiv of acetone were used.
Scheme 3
Scheme 3. Redox-Mannich Reactions with Nitroalkanes
Reactions were performed on a 0.5 mmol scale. Yields were determined by 1H NMR using an internal standard. Yields in parentheses correspond to isolated yields.
See this image and copyright information in PMC

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