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Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined ?-Arylpyrrolidines.


ABSTRACT: The synthesis of ?-arylpyrrolidines via a catalytic enantioselective intermolecular allylic C(sp)3-H functionalization of trans-alkenes followed by immediate reduction, ozonolysis, and then in situ diversification of the resulting cyclic hemiaminal to furnish highly substituted, stereoenriched ?-arylpyrrolidines is reported. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbene precursors and the dirhodium tetracarboxylate catalyst Rh2( S-NTTL)4. A variety of ?-arylpyrrolidines were prepared in good yields with high levels of diastereo- and enantioselectivity over four linear steps, requiring only a single purification procedure.

SUBMITTER: Kubiak RW 

PROVIDER: S-EPMC7232104 | BioStudies | 2018-01-01

REPOSITORIES: biostudies

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