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DOI: 10.1055/s-0030-1260979
Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones
Publication History
Publication Date:
03 August 2011 (online)
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Abstract
Mannich-type reactions with nitrones, oximes, and hydrazones provide efficient approaches to β-amino carbonyl derivatives with nitrogen functionality existing in an intermediate oxidation state, as in the cases of hydroxylamine and hydrazine derivatives. By employing chiral substrates and catalysts enantiomerically pure substances can be prepared by using these processes.
1 Introduction
2 Mannich-Type Reactions with Nitrones
2.1 Metal Enolates
2.2 Silyl Ketene Acetals
3 Mannich-Type Reactions with Oximes
4 Mannich-Type Reactions with Hydrazones
5 Concluding Remarks
Key words
Mannich bases - nitrones - hydrazones - oximes - nucleophilic addition - hydroxylamines - hydrazines
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References and Notes
N-Tosyl imines, in which a sulfur atom is directly linked to the imine nitrogen, are excluded from this Account as those compounds can be considered as a particular type of imines.
61For detailed energy values, see ref. 33.