Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution

doi:10.6023/cjoc202205037

Abstract

Kinetic resolution is an efficient and widely used asymmetric organic synthesis strategy, which can transform racemic compounds into highly optically active building blocks. It is quite an important part of modern asymmetric synthesis. Although it has long been known as a common method to gain enantioenriched raw material, kinetic resolution processes involving asymmetric catalysis often show poor resolution efficiency and limited substrates scope in practice, which greatly hinder the development of this strategy. It is not until the past two decades, with the rapid development of chiral ligands and catalysts in the field of asymmetric catalysis, that kinetic resolution strategy has been increasingly applied in the efficient separation of racemic substrates to provide versatile chiral molecules with excellent optical purity. Since the strategy of kinetic resolution was first successfully employed in the catalytic asymmetric 1,3-dipolar cycloadditions with azomethine imines in 2005, studies on 1,3-dipolar cycloadditions with efficient kinetic resolution to achieve chiral N-heterocyclic compounds or highly enantioselective fragments have been well developed. The recent progress of kinetic resolution strategy in catalytic asymmetric 1,3-dipolar cycloaddition reactions involving azomethine imines and azomethine ylides is summarized according to the different azomethine 1,3-dipoles involved, and the related limitations and development prospects are also discussed.

Key words: kinetic resolution, asymmetric 1,3-dipolar cycloaddition, azomethine imine, azomethine ylide, chiral N-heterocycle

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Huachao Liu, Chong Shen, Xin Chang, Chunjiang Wang. Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3322-3334.

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Fig. & Tab. 16

Scheme 1. Principle and equilibrium point of kinetic resolution

Scheme 2. Kinetic resolution of azomethine imines via copper (I)-catalyzed asymmetric [3+2] cycloadditions

Scheme 3. N-Heterocyclic carbene-catalyzed asymmetric [3+4] cycloadditions with azomethine imines by kinetic resolution

Scheme 4. Copper(II)-catalyzed enantioselective [3+4] cycloadditions of in situ formed azoalkenes with azomethine imines involving kinetic resolution strategy

Scheme 5. Silver(I)-catalyzed enantioconvergent [3+3] cycloadditions of electron-deficient isocyanides realizing kinetic resolution of racemic azomethine imines

Scheme 6. Kinetic resolution of racemic 3-nitro-2H-chromene derivatives catalyzed by amino thiourea catalyst

Scheme 7. Kinetic resolution of racemic 2,3-allenoates enabled by chiral phosphoric acid

Scheme 8. Cu(I)-catalyzed kinetic resolution of 2H-pyran-3(6H)-one compounds

Scheme 9. Kinetic resolution of tropane derivatives with N-metallated azomethine ylides

Scheme 10. Cu(I)-catalyzed kinetic resolution and parallel kinetic resolution of MBH acetates

Scheme 11. Kinetic resolution of cyclopentene-1,3-diones catalyzed by Ag(I)/(S)-TF-BiphamPhos 38 complex

Scheme 12. Two most commonly zwitterionic resonance forms of N-metallated azomethine ylides and 1,3-dipolar cycloadditions with divergent regioselectivities

Scheme 13. Kinetic resolution of alkylidene norcamphors via Cu(I)/(S)-TF-BiphamPhos 38 complex catalyzed regioselective 1,3-dipolar cycloadditions

Scheme 14. Facile access to the key intermediate of (+)-(Z)- and (-)-(E)-β-santalol

Scheme 15. Cu(I)-catalzyed kinetic resolution of exo- and endo-3-oxodicyclopentadienes

Scheme 16. Cu-catalyzed kinetic resolution of racemic 2H-azirines

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