Synthesis 2017; 49(15): 3255-3268
DOI: 10.1055/s-0036-1589063
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Synthesis and Chemistry of Nitronates

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
,
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
› Author Affiliations
This work was supported by the Russian Science Foundation (project 14-50-00126).
Further Information

Publication History

Received: 27 April 2017

Accepted after revision: 31 May 2017

Publication Date:
05 July 2017 (online)


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

 
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