Recent Advances on the Synthesis of β-Lactams by Involving Carbon Monoxide

doi:10.6023/cjoc202104060

Abstract

β-Lactam compounds are antibiotics with high biological activity and high application value. Design and synthesis of β-lactams with high efficiency and high selectivity have always been a hot issue in organic chemistry. Because of the carbonyl group in the ring structure, the carbonylation reaction between substrate and carbon monoxide (CO) has also developed into a new method for synthesis of β-lactams, which can be used to synthesize novel and diverse structures in one step. In this paper, the carbonylation of different substrates with CO to synthesize β-lactams in recent years is reviewed, and the existing problems and future development of this strategy are prospected.

Key words: β-lactams, carbon monoxide, carbonylation, aziridine, ketene

Cite this article

Peng Wang, Da Yang, Huan Liu. Recent Advances on the Synthesis of β-Lactams by Involving Carbon Monoxide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3448-3458.

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Fig. & Tab. 38

Scheme 1. Synthesis of β-lactams catalyzed by transition metal

Scheme 2. Carbonylation of diaziridines to β-lactams catalyzed by Cobalt

Scheme 3. Regiospecific ring expansion of aziridines to β-lactams

Scheme 4. Novel entry to 3,4-disubstituted 2-azetidinone derivative via Pd-assisted carbonylation of 2-substituted 3-vinyl- aziridine

Scheme 5. Pd-catalyzed transformation of a chiral vinylaziridine to a β-lactams

Scheme 6. First synthesis of highly strained trans-bicyclic β- lactams

Scheme 7. One-pot conversion of aziridine to β-lactam using Nickel tetracarbonyl

Scheme 8. Carbonylation of epoxides to β-lactams using [Lewis acid]+[Co(CO)4]– complexes

Scheme 9. Theoretical study of Rh(I) catalyzed carbonylative ring expansion of aziridines to β-lactams

Scheme 10. Stereoselective synthesis of trans-β-lactams by Pd-catalyzed carbonylation of vinyl aziridines

Scheme 11. Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks

Scheme 12. Mechanism for carbonylation of aziridines to β-lactams

Scheme 13. Pd-catalyzed carbonylation of allyl diethyl phosphate for synthesis of β-lactams

Scheme 14. The stereoselective synthesis of alkenyl-β-lactams by Pd-catalyzed [2+2] carbonylative cycloaddition

Scheme 15. Multicomponent synthesis of β-lactams from imines, acid chloride and carbon monoxide

Scheme 16. Stereoselective synthesis of 3,4-diaryl β-lactams

Scheme 17. Pd2(dba)3-catalyzed reactions of CO with N-tosyl- hydrazone salts and imines

Scheme 18. Pd/N-heterocyclic carbene-catalyzed carbonylation of substituted benzyl chlorides with imine to synthesize β-lactams

Scheme 19. [1+1+2] reaction for the synthesis of chiral β- lactams

Scheme 20. Reaction mechanism of synthesis of β-lactams by involving ketenes: mechanistic proposal

Scheme 21. Carbonylation of M—C bond and M=C bond to synthesize β-lactams

Scheme 22. Synthesis of β-lactams derived from the ethoxycarbonyl ketenes catalyzed by cobalt

Scheme 23. [CoII(Por)]-catalyzed trans-selective β-lactams synthesis from α-diazocarbonyl compounds

Scheme 24. Rh catalyst screening for β-lactams synthesis from carbene precursor and N-benzylidenemethanamine

Scheme 25. Access to β-lactams by enantioselective Pd(0)- catalyzed C(sp3)—H alkylation

Scheme 26. Pd-catalyzed C—H activation of aliphatic amines to give strained nitrogen heterocycles

Scheme 27. Synthesis of β-lactams by Pd(0)-catalyzed C(sp3)—H carbamoylation

Scheme 28. Pd(II)-catalyzed carbonylation of β-C—H bonds in aliphatic amines to synthesize β-lactams

Scheme 29. α-Tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of methylene β-C—H bonds to synthesize β-lactams

Scheme 30. Synthesis of β-lactams by C(sp3)—H carbonylation: mechanistic proposal

Scheme 31. Synthesis of β-lactam skeleton medical intermediate

Scheme 32. Synthesis of β-lactams from 2-bromopropenyl- amine

Scheme 33. Approach to α-silylmethylene-β-lactams via Rh- catalyzed silylcarbonylation of propargylamine derivatives

Scheme 34. Synthesis of bicyclic β-lactams via Pd/Rh-catalyzed carbonylative coupling and cyclization reactions

Scheme 35. PdCl2-catalyzed efficient transformation of propargylic amines to (E)-α-chloroalkylidene-β-lactams

Scheme 33. Synthesis of β-lactams catalyzed by rhodium nanoparticles

Scheme 37. Pd-catalyzed oxidative carbonylation of N-allyl- amines for the synthesis of β-lactams

Scheme 38. Pd-catalyzed multicomponent approach to β-lactams

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