Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions

doi:10.6023/cjoc202211032

Abstract

Chiral αα-carbonyl compounds are important structural units in natural products and pharmaceuticals and versatile synthetic building blocks in organic synthesis. Transition metal-catalyzed asymmetric acylation reaction is one of the most straightforward methods for preparing these compounds. In particular, significant progress has been made in the area of nickel-catalyzed asymmetric acylation reaction, due to the unique properties of nickel catalysts. The latest progress of nickel-catalyzed asymmetric acylation reaction, including nickel-catalyzed asymmetric alkyl-acyl cross-coupling reaction, asymmetric hydroacylation of alkene and asymmetric acyl-functionalization alkene, is summarized.

Key words: nickel catalysis, asymmetric acylation, hydroacylation, alkene

Cite this article

Yanyan Zhang, Zhuzhu Zhang, Shengqing Zhu, Lingling Chu. Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1023-1035.

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Fig. & Tab. 21

Scheme 1. Nickel-catalyzed asymmetric acylation reactions

Scheme 2. Asymmetric acylation of α-substituted lactams

Scheme 3. Asymmetric reductive coupling of acid chlorides and secondary alkyl chlorides

Scheme 4. Asymmetric reductive acylation of α-trifluoromethyl brormides

Scheme 5. Asymmetric acylation of αα-trifluoromethyl brormides

Scheme 6. Nickel/photoredox-catalyzed asymmetric acyl cross- coupling with DHPs and symmetrical anhydrides

Scheme 7. Asymmetric C—H acylation of alkylamines cataly- zed by nickel/photoredox

Scheme 8. Nickel/photoredox-catalyzed asymmetric benzylic C(sp3)—H acyltion

Scheme 9. Asymmetric hydrocarbamoylations of alkenes

Scheme 10. Three-component asymmetric reductive hydroacylation of alkenes

Scheme 11. Asymmetric migratory reductive acylation of olefins or alkyl halides

Scheme 12. Asymmetric carbamoylation of unactivated alkenes

Scheme 13. Asymmetric reductive carbamoylation of alkenes

Scheme 14. Asymmetric reductive carbo-acylation of alkenes

Scheme 15. Asymmetric reductive dicarbamoylation of alkenes

Scheme 16. Asymmetric reductive carbamoyl-alkylation of un- activated alkenes

Scheme 17. Desymmetric carbamoyl-alkylation of unactivated 1,6-dienes

Scheme 18. Asymmetric alkyl-carbamoylation of internal alkenes with alkyl iodides

Scheme 19. Asymmetric cyclization of ortho-allyl substituted arylcarbamyl chlorides with alkyl iodines

Scheme 20. Nickel/photoredox-catalyzed asymmetric acylcar- bamoylation of alkenes

Scheme 21. Asymmetric carbamoyl iodination of 1,1-disubsti- tuted styrenes

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