Asymmetric Organocatalysis and the Nitro Group Functionality

Lewis S. Aitken; Natasha R. Arezki; Antonio Dell’Isola; Alexander J. A. Cobb

doi:10.1055/s-0033-1338522

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(19): 2627-2648
DOI: 10.1055/s-0033-1338522

review

Asymmetric Organocatalysis and the Nitro Group Functionality

Lewis S. Aitken

School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK Fax: +44(118)3784644 eMail: a.j.a.cobb@reading.ac.uk

,

Natasha R. Arezki

School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK Fax: +44(118)3784644 eMail: a.j.a.cobb@reading.ac.uk

,

Antonio Dell’Isola

School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK Fax: +44(118)3784644 eMail: a.j.a.cobb@reading.ac.uk

,

Alexander J. A. Cobb*

School of Chemistry, Food and Pharmacy (SCFP), University of Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK Fax: +44(118)3784644 eMail: a.j.a.cobb@reading.ac.uk

› Institutsangaben

Abstract

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Abstract

The nitro group is an exceptionally versatile functional group, not only because it is essentially a masked amine, but also because its chemistry can be exploited in a number of useful ways. Asymmetric organocatalysis in particular has capitalized on the use of the nitro group towards the synthesis of a variety of nitrogen-containing targets. Perhaps of greatest interest is that this functional group has been shown to be invaluable within the rapidly expanding field of organocatalytic domino reactions. This review features selected examples of nitro group reactivity in organocatalysis to demonstrate its dynamism and utility.

1 Introduction

2 Nitroalkanes in Organocatalysis

2.1 Secondary Amine Catalyzed Nitronate Reactions

2.2 Brønsted Acid Catalyzed Nitronate Reactions

2.3 Phase-Transfer-Catalyzed Nitronate Reactions

3 Conjugated Nitro Compounds in Organocatalysis

3.1 Secondary Amine Catalyzed Reactions with Conjugated Nitro Compounds

3.2 Brønsted Acid Catalyzed Conjugate Additions to Nitroolefins

3.3 Phase-Transfer-Catalyzed Conjugate Additions to Nitroolefins

4 Domino Processes in Organocatalysis Using Nitroolefins

4.1 Secondary Amine Catalyzed Domino Processes

4.2 Brønsted Acid Catalyzed Domino Processes

5 Conclusions

Key words

organocatalysis - nitro group - conjugate addition - nucleophilic addition - cyclization - cascade reaction - domino reaction

Volltext

Referenzen

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