Asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines via an organocatalytic domino Michael/Mannich [3+2] cycloaddition.

doi:10.1039/C6CC08352H

Paper

Asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines via an organocatalytic domino Michael/Mannich [3+2] cycloaddition.

Published Nov 29, 2016 · Ying Zhi, Kun Zhao, Qiang Liu

Chemical communications

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21

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Abstract

The asymmetric synthesis of highly functionalized pyrrolidine derivatives with three contiguous stereogenic centers and bearing a trifluoromethyl group has been developed through an organocatalytic domino Michael/Mannich [3+2] cycloaddition sequence. Employing a commercially available secondary amine as the catalyst, the scalable one-pot protocol occurs with high yields and excellent stereoselectivities, providing a short entry into a series of trifluoromethylated pyrrolidines with potential medical value.

Study Snapshot

The organocatalytic domino Michael/Mannich [3+2] cycloaddition method enables the asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines with high yields and excellent stereoselectivities, offering potential medical value.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines via an organocatalytic domino Michael/Mannich [3+2] cycloaddition.

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References

Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.

This scalable domino reaction allows for the synthesis of 4-phenyl-substituted chromans with spiro-connected oxindole scaffolds and high stereoselectivities in good to excellent yields.

Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro-1,2-Diazepinones by NHC-Catalyzed [3+4] Annulation Reactions.

NHC-catalyzed [3+4] annulation reactions enable the asymmetric synthesis of spirobenzazepinones, spiro-1,2-diazepinones, and spiro-1,2-oxazepinones with high yields and

Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones.

This copper(I)-catalyzed reaction efficiently accesses highly substituted pyrrolidines with a trifluoromethylated, all-carbon quaternary stereocenter in good yields, with up to 20:1 d.r. and 98 % ee.

Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides.

Silver-catalyzed 1,3-dipolar cycloaddition of fluorinated azomethine ylides and activated olefins offers a straightforward and atom-economical method for the preparation of fluorinated pyrrolidines with high diaste

Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3'-oxindole] framework.

This study demonstrates a catalytic asymmetric chemoselective 1,3-dipolar cycloaddition of an azomethine ylide with imines, enabling the first enantioselective construction of a spiro[imidazol

Citations

Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones

This research developed a metal-free diastereoselective formal 1,3-dipolar cycloaddition method for efficient desymmetrization of cyclopentene-1,3-diones, leading to the production of tetracyclic spirooxind

CAN Combined with NaI as Promoter System for the Synthesis of Novel Ethyl 1,2-Diarylpyrrolidine-3-carboxylate Derivatives via Three-Component Reaction

CAN and NaI as promoter systems allows for the efficient synthesis of novel ethyl 1,2-diarylpyrrolidine-3-carboxylate derivatives in biologically active compounds and valuable synthetic intermediates.

Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells

This study demonstrates a novel synthesis method for 2,3′-spirobi (indolin)-2′-ones, which may trigger mitophagy in cancer cells by changing mitochondrial morphology and inducing mitophagy.

Dinuclear zinc-catalyzed enantioselective formal [3 + 2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with low reactivity aurone derivatives.

Dinuclear zinc catalysts enable efficient construction of chiral spiro[benzofuran-pyrrolidine] scaffolds with high yields and enantioselectivity, potentially benefiting biological research.

Organocatalytic synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols: asymmetric oxa-1,3-dipolar cycloaddition of trifluoroethylamine-derived azomethine ylides

This study developed a catalytic method for the facile synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols with excellent yields and diastereoselectivities, offering potential for medicinal chemistry applications.