Recent Progress in (3+3) Cycloadditions of Bicyclobutanes to Access Bicyclo[3.1.1]heptane Derivatives

Dedicated to Professor Junliang Zhang on the occasion of his 50th birthday.

Abstract

The synthesis of bicyclo[3.1.1]heptane (BCHeps) derivatives, which serve as three-dimensional (3D) bioisosteres of benzenes and are the core skeleton of several terpene natural products, is garnering growing interest. The (3+3) cycloadditions of bicyclobutanes (BCBs) represent an attractive method for efficiently accessing (hetero)BCHep skeletons with 100% atom economy. Herein, we give a brief summary of recent achievements in this approach for the synthesis of diverse BCHep derivatives, emphasizing our recent progress in the initial palladium-catalyzed (3+3) cycloadditions of bicyclobutanes with vinyl oxiranes.

1 Introduction

2 Radical (3+3) Cycloaddition Reaction

3 Polar (3+3) Cycloaddition Reaction

4 Palladium-Catalyzed Enantioselective (3+3) Cycloaddition Reaction

5 Conclusion

Key words

strained molecules - bicyclic compounds - cycloaddition - palladium - σ-bond metathesis

Publication History

Received: 17 July 2024

Accepted after revision: 28 August 2024

Accepted Manuscript online:
28 August 2024

Article published online:
08 October 2024

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