Recent Advances in Transition-Metal-Catalyzed (4+3)-Cycloadditions

Heather Lam; Mark Lautens

doi:10.1055/s-0039-1690875

Synthesis, Table of Contents

Synthesis 2020; 52(17): 2427-2449
DOI: 10.1055/s-0039-1690875

review

Recent Advances in Transition-Metal-Catalyzed (4+3)-Cycloadditions

Authors

Heather Lam
Mark Lautens ∗

Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada Email: mark.lautens@utoronto.ca

Abstract

All articles of this category

Dedicated to the 50^th anniversary of SYNTHESIS

Abstract

A (4+3)-cycloaddition combines a four-atom synthon and three-atom synthon to form seven-membered rings. In the past decade, many improvements have been made to this class of cycloaddition, including excellent diastereo- and enantioselectivities, both intra- and intermolecularly. Through the strategic use of transition-metal catalysts, acids, bases, and organocatalysts, it is possible to perform the cycloaddition on a variety of substrates, generating novel seven-membered rings. With these advances, (4+3)-cycloaddition has also been applied to the synthesis of biologically relevant compounds and natural products. We exclude the cycloadditions of cyclic dienes such as furan, pyrrole, cyclohexadiene or cyclopentadiene as Chiu, Harmata, Mascareñas and others have recently published thorough reviews on that topic. We will however discuss the recent additions (2009–2020) to the literature for the (4+3)-cycloadditions involving other types of four-atom synthons.

1 Introduction

2 Rhodium

2.1 Cyclopropanation/Cope Rearrangement

2.2 C–H activation

3 Gold, Silver

4 Copper

5 Palladium, Platinum, Iridium

6 Dual-Activation

7 Conclusion

Key words

(4+3)-cycloaddition - annulation - transition-metal catalysis

Full Text

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