Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions

doi:10.6023/cjoc202207036

Abstract

Transition metal-catalyzed hydroacylation reaction of aldehydes with π-unsaturated compounds provides an economical and efficient method for the construction of C—C bonds, not only allowing readily available starting materials to be used as substrates, but also featuring high atom and step economy. Therefore, the reaction has received continuous and extensive attention during the past several decades. The advances on enantioselective transition metal-catalyzed hydroacylation reactions are summarized, focusing on reaction types, asymmetric strategies and reaction mechanisms.

Key words: transition metal catalysis, hydroacylation, asymmetric catalysis, aldehydes, alkenes

Cite this article

Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.

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Fig. & Tab. 43

Scheme 1. Transition metal-catalyzed hydroacylations

Scheme 2. Hydroacylation of 4-pentenal catalyzed by stoichiometric metals

Scheme 3. Asymmetric hydroacylation of 2-disubstituted 4-pentenal

Scheme 4. Asymmetric hydroacylation of 4-substituted 4-pentenals

Table 1. Asymmetric hydroacylation of 4-pentenal via cationic Rh catalyst

Table 2. Rh-catalyzed desymmetric hydroacylation of 4-pentenals

Scheme 5. Rh-catalyzed asymmetric hydroacylation of 3-subs- tituted 4-pentenals via kinetic resolution

Scheme 6. Rh-catalyzed asymmetric hydroacylation of 4-pentenals via kinetic resolution

Scheme 7. Asymmetric hydroacylation of 4-pentenals

Scheme 8. Rh-catalyzed isohydroacylation of 2,2-disubstituted 4-pentenals

Scheme 9. Co-catalyzed hydroacylation of 2,2-disubstituted 4- pentenals

Scheme 10. Dynamic kinetic-resolution hydroacylation

Table 3. Enantioselective DKR hydroacylation

Scheme 11. Dynamic kinetic-resolution hydroacylation

Scheme 12. Asymmetric hydroacylation of 3-pentenals

Table 4. Kinetic resolution of 4-alkynals

Scheme 13. Parallel kinetic resolution of 4-alkynals

Scheme 14. Desymmetrization of dioxocyclohexane

Scheme 15. Hydroacylation of 2-vinyl benzaldehydes

Scheme 16. Rh-catalyzed asymmetric hydroacylation of aromatic aldehydes with ketones

Scheme 17. Co-catalyzed asymmetric hydroacylation of alkenes or ketones

Scheme 18. Rh-catalyzed hydroacylation

Scheme 19. Hydroacylation via cooperative catalysis of iminium-ion and transition-metal

Scheme 20. Rh-catalyzed asymmetric hydroacylation of 1,1,2- trisubstituted alkenes

Scheme 21. Co-catalyzed asymmetric hydroacylation of 1,1,2- trisubstituted alkenes

Scheme 22. Asymmetric hydroacylation of o-(2-alkylvinyl)benzaldehydes

Scheme 23. Ir-catalyzed asymmetric hydroacylation of aromatic aldehydes with ketones

Scheme 24. Rh-catalyzed hydroacylation for synthesis of nitrogen-containing six-membered ring

Scheme 25. Rh-catalyzed enantioselective hydroacylation of ortho-allylbenzaldehydes

Scheme 26. Rh-catalyzed hydroacylation for synthesis of medium-sized ring

Scheme 27. Rh-catalyzed hydroacylation of ketones for synthesis of medium-sized ring

Scheme 28. Metal-organic cooperative catalysis for medium-ring synthesis

Scheme 29. Asymmetric hydroacylation of salicylaldehydes with norbornadienes

Scheme 30. Asymmetric hydroacylation of 1,3-disubstituted allenes with β-S-substituted aldehydes

Scheme 31. Asymmetric hydroacylation of homoallylic salicylaldehydes with sulfides

Scheme 32. Asymmetric hydroacylation of salicylaldehydes with cyclopropenes

Scheme 33. Asymmetric hydroacylation of salicylaldenhydes with cyclobutenes

Scheme 34. Asymmetric hydroacylation of hexadienes

Scheme 35. Asymmetric hydroacylation of acrylamides and aldehydes

Scheme 36. Asymmetric hydroacylation of ketoamides and aldehydes

Scheme 37. Asymmetric hydroacylation of ketoamides and aldehyde

Scheme 38. Asymmetric hydroacylation of 1,6-enynes and aldehydes

Scheme 39. Asymmetric hydroacylation of 1,3-dienes and aldehydes

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