Research Progress on Copper-Catalyzed Asymmetric Synthesis of Chiral Organophosphorus Compounds

doi:10.6023/cjoc202405002

Abstract

Chiral organophosphorus compounds have a wide range of application in the fields of medicine, pesticides, and functional materials, and also serve as versatile ligands or organocatalysts in asymmetric catalysis. Therefore, their asymmetric synthesis has attracted an increasing attention from chemists and has become one hot research topic in recent years. Asymmetric P—C or P—N bond formation by using organophosphorus compounds bearing P—H bond and various electrophilic partners serves as a straightforward and powerful strategy for constructing chiral organophosphorus compounds. The recent progress in asymmetric synthesis of chiral organophosphorus compounds catalyzed by chiral copper complexes or copper/organocatalyst co-catalytic systems is summarized. P-Chiral or/and backbone chiral organophosphorus compounds were obtained in these reactions. This paper is divided into two sections based on whether the valence state of copper is changed or not during the reaction process. Aside from the substrate scopes, the mechanisms and potential applications of some representative methodologies are also included.

Key words: copper catalysis, asymmetric synthesis, chiral organophosphorus compounds, P-chirality

Cite this article

Hui Li, Liang Yin. Research Progress on Copper-Catalyzed Asymmetric Synthesis of Chiral Organophosphorus Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3575-3586.

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Fig. & Tab. 18

Scheme 1. Stereoselective reaction of secondary phosphines or their oxides with electrophiles

Scheme 2. Epimerization of metal-phosphido species derived from secondary phosphines

Scheme 3. Tautomerization of secondary phosphine oxides

Scheme 4. Valence state change of copper catalysts

Scheme 5. N-Heterocyclic carbene-copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones

Scheme 6. Copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

Scheme 7. Copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated esters

Scheme 8. Copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated phosphine sulfides

Scheme 9. Copper-catalyzed asymmetric hydrophosphination of alkenyl isoquinolines

Scheme 10. Copper-catalyzed asymmetric hydrophosphination of 3,3-disubstituted cyclopropenes

Scheme 11. Mechanism of asymmetric hydrophosphination of 3,3-disubstituted cyclopropenes

Scheme 12. Copper and CPA co-catalyzed asymmetric hydrophosphinylation of 1-ethynylnaphthalen-2-ols

Scheme 13. Copper-catalyzed asymmetric alkylation of unsymmetrical diarylphosphines

Scheme 14. Copper-catalyzed asymmetric arylation of secondary phosphine oxides with diaryliodonium salts

Scheme 15. Copper-catalyzed asymmetric intramolecular C-P cross-coupling/cyclization

Scheme 16. Copper-catalyzed asymmetric cross-coupling of secondary phosphine oxides and aromatic iodides

Scheme 17. Copper-catalyzed asymmetric Michaelis-Becker- type cross-coupling reaction

Scheme 18. Copper-catalyzed asymmetric amination of unsymmetrical diarylphosphines

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