Enantiopure Cyclic Nitrones: A Useful Class of Building Blocks for Asymmetric Syntheses

Julia Revuelta; Stefano Cicchi; Andrea Goti; Alberto Brandi

doi:10.1055/s-2007-965914

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Synthesis 2007(4): 485-504
DOI: 10.1055/s-2007-965914

REVIEW

Enantiopure Cyclic Nitrones: A Useful Class of Building Blocks for Asymmetric Syntheses

Julia Revuelta^a,b, Stefano Cicchi^a, Andrea Goti^a, Alberto Brandi*^a
^a Dipartimento di Chimica Organica ‘Ugo Schiff’, HeteroBioLab, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
Fax: +39(055)4573531; e-Mail: alberto.brandi@unifi.it;
^b Instituto de Quimica Organica General - CSIC, Grupo de Quimica Organica Biologica, C/ Juan de la Cierva 3, 28006 Madrid, Spain

Further Information

Publication History

Received 2 December 2006
Publication Date:
29 January 2007 (online)

Abstract
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Abstract

The synthesis of enantiopure cyclic nitrones has become a frequently addressed topic in discussions of their usefulness in the production of natural products and biologically active compounds. This emphasis has stimulated the development of a variety of synthetic approaches that are described in this review, organized on the basis of the size of the nitrone ring.

1 Introduction

2 Four-Membered Cyclic Nitrones

3 Five-Membered Cyclic Nitrones

3.1 Oxidation of Hydroxylamines, Amines, and Imines

3.2 Condensation of Ketones with Hydroxylamines

3.3 N-Alkylation of Oximes

4 Six-Membered Cyclic Nitrones

4.1 Oxidation of Amines and Imines

4.2 N-Alkylation of Oximes

4.3 Condensation of Carbonyl Compounds with Hydroxylamines

4.4 [4+2]-Cycloaddition Reactions

4.5 Hydroxylamine-Alkyne Cyclizations

5 Seven-Membered Cyclic Nitrones

6 Conclusion

Key words

cyclization - asymmetric synthesis - heterocycles - nitrones - enantiomerically pure compounds

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Soldaini, G.; Cardona, F.; Goti, A. manuscript submitted.