Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Austin Pounder; Eric Neufeld; Peter Myler; William Tam

doi:10.3762/bjoc.19.38

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Beilstein J Org Chem. 2023 Apr 24:19:487-540. doi: 10.3762/bjoc.19.38. eCollection 2023.

Authors

Austin Pounder¹, Eric Neufeld¹, Peter Myler¹, William Tam¹

Affiliation

¹ Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.

Abstract

This review presents a comprehensive overview of transition-metal-catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds are important synthons in organic synthesis, providing an important platform for the construction of biologically/medicinally significant compounds which bear multiple stereocenters. The review has been divided according to the metal used in the reaction. An overview of the substrate scope, reaction conditions, and their potential applications in organic synthesis is discussed. A comprehensive outlook on the reactivity paradigms of homo- and heterobicyclic alkenes is discussed and should shed light on future directions for further development in this field.

Keywords: bicyclic alkenes; cascade; catalysis; domino; transition-metal-catalyzed.

Publication types

Review

Grants and funding

This work was supported by a Discovery Grant (WT) from the Natural Sciences and Engineering Research Council (NSERC) of Canada. AP also acknowledges NSERC for financial support through the PGS-D Scholarship.