Advances in organocatalysis of the Michael reaction by tertiary Phosphines

ABSTRACT

Tertiary phosphines have been recognized as powerful organocatalysts for the Michael reaction, which is one of the most important atom-economical methods for carbon-carbon and carbon-heteroatom bond construction. In the presence of tertiary phosphines, a vast array of Michael acceptors and Michael donors can be coupled with each other under neutral and metal-free conditions to produce useful densely functionalized molecules. This review highlights the role of phosphine-catalyzed Michael reaction in cutting-edge areas, such as asymmetric synthesis, natural products synthesis, drug design, and polymer material science. As the central part of catalysis science, the kinetic and mechanistic issues are also discussed when possible. The review is organized by the type of the Michael acceptor and the Michael donor used in the reaction.

KEYWORDS:

• Tertiary phosphines
• organocatalysis
• conjugate addition
• asymmetric catalysis
• phosphonium enolates
• zwitterions

Acknowledgments

This work was supported by the Kazan Federal University Strategic Academic Leadership Program.

Disclosure statement

No potential conflict of interest was reported by the author(s).