Recent Advances in the Synthesis and Chemistry of Nitronates

This paper is dedicated to Professor Herbert Mayr on the occasion of his 70^th birthday

Abstract

Due to their availability and versatile reactivity, nitronates have become important building blocks in the stereoselective synthesis of bioactive molecules. This short review provides a summary of recent developments on the synthesis, chemistry and applications of O-alkyl and O-silyl nitronates.

1 Introduction

2 Approaches to the Synthesis of Nitronates

2.1 Synthesis of Six-Membered Cyclic Nitronates

2.1.1 Formal [4+2] Approaches

2.1.2 Formal [3+3] Approaches

2.1.3 Other Approaches

2.2 Synthesis of Five-Membered Cyclic Nitronates

2.2.1 Formal [3+2] Approaches

2.2.2 Formal [4+1] Approaches

2.2.3 Oxidation Approaches

3 Chemistry of Nitronates

3.1 Nitronates as α-C-Nucleophiles

3.2 Nitronates as α-C-Electrophiles

3.3 Nitronates in [3+n]-Annulation Reactions

3.4 Reactions Involving the β-Carbon Atom of Nitronates

3.5 Miscellaneous Transformations

4 Conclusion

Key words

nitronates - nitroalkanes - cycloaddition - 1,3-dipoles - umpolung

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