Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis

doi:10.6023/cjoc202211043

Abstract

Transition metal palladium-catalyzed asymmetric reaction is an important and efficient method to synthesize chiral compounds. It has made considerable progress and achieved great success in the past decades. However, some reactions could not achieve high reactivity and excellent stereoselectivity just promoted by transition metal palladium catalysis. Therefore, it is of great significance to combine transition metal palladium catalysis and organocatalysis, which could be conducive to dissolve these challenging problems and received great attention. In recent years, a variety of asymmetric catalytic reactions have been efficiently realized by the synergistic catalysis system of transition metal palladium catalysis and chiral phosphoric acids with high chemo-, regio-, and stereoselectivity, and considerable research results and some important breakthroughs have been achieved. The recent progress of asymmetric allylation reaction, C(sp³)—H, C(sp²)—H functionalization and other reactions promoted by this synergistic catalysis system is summarized, the interaction between catalysts and substrates is systematically analyzed, and the influence factors of reactivity and selectivity are deeply discussed.

Key words: synergistic catalysis, Pd catalysis, chiral phosphoric acid, chiral compound, stereoselectivity

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Xun Xiang, Zhaolin He, Xiuqin Dong. Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 791-808.

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Fig. & Tab. 38

Scheme 1. Pd/chiral phosphoric acid-catalyzed enantioselective α-allylic alkylation of α-branched aldehydes

Scheme 2. Possible mechanism of enantioselective α-allylic alkylation of α-branched aldehydes

Scheme 3. Asymmetric α-allylation of aldehydes with simple allylic alcohols

Scheme 4. Pd/chiral phosphoric acid catalyzed asymmetric allylic alkylation of pyrazol-5-ones

Scheme 5. Proposed catalytic cycle for the asymmetric allylic alkylation of pyrazol-5-ones

Scheme 6. Enantioselective amination of racemic allylic alcohols

Scheme 7. Enantioselective α-allylation of ketones

Scheme 8. Possible mechanism of asymmetric ketone enantioselective α-allylation

Scheme 9. Ternary catalysis enabled three-component asymmetric allylic alkylation reaction

Scheme 10. Pd/chiral phosphoric acid-catalyzed asymmetric allylic C—H activation to access chiral spirocyclic rings

Scheme 11. Pd-catalyzed asymmetric arylation of secondary β-C(sp3)—H bonds of 8-aminoquinoline amides

Scheme 12. Stereoselective carbonyl allylation with simple olefins promoted by Pd-catalyzed C—H oxidative borylation

Scheme 13. Asymmetric allylic C—H alkylation of terminal olefins with pyrazol-5-ones through cooperative catalysis of palladium complex and CAP

Scheme 14. Allylic C—H alkylation of substituted 1,4-pentadienes with pyrazol-5-ones and its synthetic application

Scheme 15. Pd-catalyzed asymmetric benzylic C—H arylation of amines

Scheme 16. Enantioselective Pd(II)-catalyzed C—H amination reaction

Scheme 17. Pd-catalyzed asymmetric C(sp3)—H arylation reaction

Scheme 18. Enantioselective α-C—H arylation of thioamides

Scheme 19. Pd-catalyzed asymmetric allylic C—H alkylation of 1,4-dienes with aldehydes

Scheme 20. Pd-catalyzed enantioselective arylation of methylene C(sp3)—H bonds

Scheme 21. Enantioselective β-C—H functionalization of thioamides

Scheme 22. Enantioselective intramolecular arylation of C(sp3)—H bonds

Scheme 23. Pd-catalyzed asymmetric C—H arylation for the synthesis of planar chiral ferrocenes

Scheme 24. Pd-catalyzed asymmetric C—H bond activation for the synthesis of P?stereogenic dibenzophospholes

Scheme 25. Enantioselective synthesis of biaryl atropisomers by Pd-catalyzed C—H olefination

Scheme 26. Synthesis of axially chiral biaryl-2-amines via Pd-catalyzed asymmetric C—H allylation

Scheme 27. Synthesis of axially chiral biaryl-2-amines via Pd-catalyzed asymmetric C—H olefination

Scheme 28. Atroposelective synthesis of conjugated diene-based axially chiral styrenes via Pd-catalyzed alkenyl C—H olefination

Scheme 29. Pd-catalyzed atroposelective C—H olefination and allylation reaction

Scheme 30. Synthesis of diaxially chiral biaryls

Scheme 31. Asymmetric cascade annulation based on oxa- Diels-Alder cycloaddition

Scheme 32. Enantioselective aryl borylation of alkene

Scheme 33. Possible mechanism of enantioselective aryl boration of alkenes

Scheme 34. Enantioselective diarylation of benzyl acrylate

Scheme 35. Asymmetric Heck-Matsuda arylation of cyclic alkenes and aryl diazonium salts

Scheme 36. Possible mechanism of Pd-catalyzed asymmetric Heck- Matsuda arylation of cyclic alkenes and aryl diazonium salts

Scheme 37. Asymmetric Heck-Matsuda arylation of spirocyclic alkenes and aryl diazonium salts

Scheme 38. Pd-catalyzed asymmetric α-alkylation of azlactones with nonconjugated alkenes

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