Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides

doi:10.6023/cjoc202212024

Abstract

Enantioenriched organophosphates are ubiquitous in a large array of chiral ligands, chiral catalysts and bioactive molecules. Over the past few decades, synthetic chemists have contributed substantial efforts to develop the efficient methodologies for the construction of P-chiral phosphine derivatives, considerably enriching the arsenal of chiral organophosphine ligands and the promising pharmaceutical molecules. Among them, a number of works are focused on the synthesis of P-chiral phosphine oxides because it is more stability than trivalent phosphines and the convenient reduction. In view of the rapid progress in this area and the currently available reviews, the progress in the last three years is summarized and discussed, namely from 2020 to 2022. The description of the synthetic strategy is divided into five segments, involving asymmetric induction, catalytic desymmetrization, catalytic asymmetric synthesis, catalytic kinetic resolution or dynamic kinetic asymmetric transformation, and enzyme catalysis.

Key words: P-chiral phosphine oxides, organic phosphine ligands, asymmetric synthesis, asymmetric catalysis, kinetic resolution

Cite this article

Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.

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Fig. & Tab. 23

Scheme 1. Chiral phosphine ligands

Scheme 2. Synthesis of P-chiral diphosphine ligands assisted with chiral auxuliary

Scheme 3. Synthesis strategy of P-chiral phosphine oxide

Scheme 4. Synthesis of P-chiral phosphine oxide assisted by chiral amino alcohols

Scheme 5. Visible light induced synthesis of P-chiral phosphine oxides

Scheme 6. Construction of P-chiral phosphine oxide containing axial chirality using BINOL as chiral auxiliary

Scheme 7. Construction of P-chiral phosphine oxide by asymmetric halogenation

Scheme 8. Construction of P-chiral phosphine oxide via asymmetric bromination

Scheme 9. Construction of P-chiral phosphine oxides by asymmetric boration

Scheme 10. Catalytic desymmetry for synthesis of axially and P-chiral phosphine oxides by a chiral amide and an achiral Cp*Ir

Scheme 11. Construction of P-chiral phosphine oxides by cobalt/salax-catalyzed alkoxylation/amination

Scheme 12. Asymmetric construction of P-chiral phosphine oxides of phosphonates and alkynes

Scheme 13. Highly chemo-, regio-, and enantio-selective construction of P-chiral alkenylphosphine oxides using secondary phosphine oxides

Scheme 14. Ni-catalyzed enantioselective allyl alkylation

Scheme 15. Nickel catalyzed enantioselective benzylation of SPOs

Scheme 16. Asymmetric alkylation of secondary phosphine oxides catalyzed by chiral cobalt complex

Scheme 17. Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes

Scheme 18. Enantioselective synthesis of P-stereogenic alenylphosphine oxides through Ni-catalysed propargylic substituion

Scheme 19. Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos catalyzed kinetic resolution

Scheme 20. Pd/Xiao-Phos-catalyzed kinetic resolution of SPOs

Scheme 21. Copper catalyzed DYKAT construction of cyclic P-chiral phosphine oxide

Scheme 22. Enzymatic catalytic synthesis of remdesivir

Scheme 23. Enzymatic desymmetry construction of phosphine oxides or sulfides

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