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

Affron, Dominic P ; Davis, Owen A ; Bull, James A

Organic letters, 2014-09, Vol.16 (18), p.4956-4959 [Periódico revisado por pares]

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Título:
Regio- and Stereospecific Synthesis of C‑3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)–H Arylation
Autor: Affron, Dominic P ; Davis, Owen A ; Bull, James A
Assuntos: Biological Products - chemical synthesis ; Biological Products - chemistry ; Catalysis ; Combinatorial Chemistry Techniques ; Hydrocarbons, Iodinated - chemistry ; Molecular Structure ; Palladium - chemistry ; Proline - analogs & derivatives ; Proline - chemical synthesis ; Proline - chemistry ; Pyrrolidines - chemistry ; Stereoisomerism
É parte de: Organic letters, 2014-09, Vol.16 (18), p.4956-4959
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: 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.
Editor: United States: American Chemical Society
Idioma: Inglês

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