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Regio- and Stereospecific Synthesis of C‑3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)–H Arylation

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journal contribution
posted on 17.12.2015, 04:41 by Dominic P. Affron, Owen A. Davis, James A. Bull
Functionalization of C­(sp3)–H bonds at the unactivated 3-position of proline derivatives has been achieved using aryl iodides and palladium catalysis. This directly affords cis-2,3-disubstituted pyrrolidines as single stereoisomers. 3-Arylation occurs in high yield under solvent-free conditions with amino­quinoline and methoxy­amino­quinoline directing groups. The latter was readily removed to give primary amide derivatives with physicochemical properties appropriate for use as fragments in drug discovery.