Recent Advances in the Synthesis and Chemistry of Nitronates

Andrey A. Tabolin; Alexey Yu. Sukhorukov; Sema L. Ioffe; Alexander D. Dilman

doi:10.1055/s-0036-1589063

Synthesis, Table of Contents

Synthesis 2017; 49(15): 3255-3268
DOI: 10.1055/s-0036-1589063

short review

Recent Advances in the Synthesis and Chemistry of Nitronates

Authors

Andrey A. Tabolin

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation Email: sukhorukov@ioc.ac.ru Email: adil25@mail.ru
Alexey Yu. Sukhorukov*

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation Email: sukhorukov@ioc.ac.ru Email: adil25@mail.ru
Sema L. Ioffe

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation Email: sukhorukov@ioc.ac.ru Email: adil25@mail.ru
Alexander D. Dilman *

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation Email: sukhorukov@ioc.ac.ru Email: adil25@mail.ru

Abstract

All articles of this category

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

Full Text

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