Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade

Ying Xu; Ling Li; Min Zhao; Yaojia Jiang

doi:10.1055/a-1983-1750

Synlett, Table of Contents

Synlett 2023; 34(04): 293-300
DOI: 10.1055/a-1983-1750

synpacts

Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade

Authors

Ying Xu

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China
Ling Li

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China
Min Zhao

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China
Yaojia Jiang∗

^aLaboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, P. R. of China

^bInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China

Abstract

All articles of this category

Abstract

The reassembly of unsaturated C–C bonds has attracted widespread attention from synthetic chemists due to its advantages of unique reactivity, easy handling, and high atom and step economies. We recently explored a cutting/insertion cascade as a means of introducing a new C₁ source and constructing functionalized 1,4-keto aldehyde and 2H-furan derivatives through cyclopropanation of enamines with various carbene precursors and subsequent ring-opening reactions in situ. Aminocyclopropanes are believed to be involved as key intermediates in these transformations. This Synpacts article outlines our recent contributions to this increasingly important research area.

1 Introduction

2 Cleavage of Enamine C=C Double Bonds and Hydrolysis to 1,4-Keto Aldehydes

3 Cleavage of Enamine C=C Double Bonds and Cyclization to 2H-Furans

4 Cleavage of Ynone/Ynoate C≡C Triple Bonds

5 Conclusion

Key words

carbenes - enamines - cascade reaction - cyclopropanes - keto aldehydes - furans

Full Text

References

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