Recent Developments in Transannular Reactions

Dedicated to Prof. Dr. Joan Bosch on the occasion of his 75^th birthday

Abstract

Transannular reactions have shown a remarkable performance for the construction of polycyclic scaffolds from medium- or large-sized cyclic molecules in an unconventional manner. Recent examples of transannular reactions reported from 2011 have been reviewed, emphasizing the excellent performance of this approach when accessing the target compounds. This review also highlights how this methodology provides an alternative approach to other commonly used strategies for the construction of cyclic entities such as cyclization or cycloaddition reactions.

1 Introduction

2 Transannular Cycloadditions and Electrocyclizations

3 Transannular Conjugate Additions

4 Transannular 1,2-Addition to Ketones, Imines, Esters, and Amides

5 Transannular Reactions via Electrophilic Activation of Olefins

6 Transannular Ring-Opening of Epoxides

7 Transannular Alkylations of Enolates and Related Species

8 Miscellaneous Transannular Reactions

9 Concluding Remarks

Key words

transannular reaction - bicyclic compounds - cyclization - fused-ring systems - heterocycles - macrocycles - natural products - total synthesis

Publication History

Received: 28 March 2022

Accepted after revision: 04 May 2022

Accepted Manuscript online:
04 May 2022

Article published online:
21 July 2022

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