Mannich-Type Reactions of
Nitrones, Oximes, and Hydrazones

Pedro Merino; Tomás Tejero

doi:10.1055/s-0030-1260979

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Synlett 2011(14): 1965-1977
DOI: 10.1055/s-0030-1260979

ACCOUNT

Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones

Pedro Merino*, Tomás Tejero
Laboratorio de Síntesis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, Campus San Francisco, 50009 Zaragoza, Aragón, Spain
Fax: +34(976)762075; e-Mail: pmerino@unizar.es;

Further Information

Publication History

Received 23 March 2011
Publication Date:
03 August 2011 (online)

Abstract
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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

References and Notes

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61

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