Recent Advances in the Synthesis and Chemistry of Nitronates

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 Introduction2 Approaches to the Synthesis of Nitronates2.1 Synthesis of Six-Membered Cyclic Nitronates2.1.1 Formal [4+2] Approaches2.1.2 Formal [3+3] Approaches2.1.3 Other Approaches2.2 Synthesis of Five-Membered Cyclic Nitronates2.2.1 Formal [3+2] Approaches2.2.2 Formal [4+1] Approaches2.2.3 Oxidation Approaches3 Chemistry of Nitronates3.1 Nitronates as α-C-Nucleophiles3.2 Nitronates as α-C-Electrophiles3.3 Nitronates in [3+n]-Annulation Reactions3.4 Reactions Involving the β-Carbon Atom of Nitronates3.5 Miscellaneous Transformations4 Conclusion