Recent Advances in the Synthesis and Chemistry of Nitronates

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