Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes

doi:10.6023/cjoc202302010

Abstract

Because of the broad substrate availability, high atom economy and efficient stereocontrol, palladium-catalzyed asymmetric hydrofunctionalizations of conjugated dienes have emerged as an efficient route to construct enantioenriched allylic motifs, including allylic C—C, C—N, C—S, C—P, C—Si and C—O bonds. The development, advance and mechanistic features of this area in the past decades are summarized. Based on the types of allylic stereogenic centers constructed via this strategy, the review is divided into six parts, including asymmetric hydroalkylation, hydroamination, hydrophosphinylation, hydrosulfonylation, hydrosilylation and hydroalkoxylation.

Key words: palladium catalysis, conjugated dienes, hydrofunctionalization, asymmetric synthesis

Cite this article

Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.

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Fig. & Tab. 30

Scheme 1. Mechanistic characters for palladium-catalyzed asymmetric hydrofunctionalizations of conjugated dienes

Scheme 2. The first enantioselective hydroalkylation of 1,3- dienes

Scheme 3. Pd-PHOX-catalyzed asymmetric hydroalkylation of conjugated dienes

Scheme 4. Asymmetric hydroalkylation of non-terminal dienes

Scheme 5. Plausible mechanism for asymmetric hydroalkylation of internal dienes

Scheme 6. The construction of quaternary stereogenic centers

Scheme 7. Asymmetric hydroalkylation of conjugated dienes with azlactones

Scheme 8. Pd(OAc)2 catalyzed asymmetric hydroalkylation of 1,3-dienes with azlactones

Scheme 9. Stereoselective synthesis of homoallylic α?trifluoro- methyl amines

Scheme 10. Pd/Cu-catalyzed stereodivergent hydroalkylation of conjugated dienes with aldimine esters

Scheme 11. Synergistic Pd/amine-catalyzed stereodivergent hy- droalkylation of conjugated dienes with aldehydes

Scheme 12. Synergistic Pd/Lewis base-catalyzed stereodivergent hydroalkylation of conjugated dienes with pentafluorophenyl acetates

Scheme 13. Synergistic palladium/PTC-catalyzed stereodivergent hydroalkylation of conjugated dienes

Scheme 14. Umpolung asymmetric 1,5-conjugate additions via palladium hydride catalysis

Scheme 15. The first asymmetric hydroamination of conjugated dienes with aromatic amines

Scheme 16. Asymmetric hydroamination of linear conjugated dienes with aliphatic amines

Scheme 17. Asymmetric hydroamination of internal dienes with amines

Scheme 18. Proposed mechanism for hydroamination of internal dienes

Scheme 19. Asymmetric hydroamination of conjugated dienes with pyrazoles

Scheme 20. Asymmetric hydrophosphinylation of conjugated dienes with phosphine oxides

Scheme 21. Asymmetric hydrosulfonylation of conjugated dienes with sulfinic acids

Scheme 22. Asymmetric hydrosulfonylation of conjugated dienes with sulfonyl hydrazides

Scheme 23. Proposed mechanism for asymmetric hydrosulfonylation

Scheme 24. The first asymmetric hydrosilylation of cyclopentadiene

Scheme 25. Asymmetric hydrosilylation of cyclopentadiene and cyclohexadiene

Scheme 26. Asymmetric hydrosilylation of cyclic dienes in Hayashi group

Scheme 27. Asymmetric hydrosilylation of linear dienes

Scheme 28. Pd-catalyzed asymmetric hydroalkoxylation of conjugated dienes

Scheme 29. Proposed mechanism for asymmetric hydroalkoxylation

Scheme 30. Pd-catalyzed asymmetric hydration and hydroaminoxylation of conjugated dienes

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