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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