Regio- and Stereospecific Synthesis of C-3 Functionalized Proline Derivatives by Palladium Catalyzed Directed C(sp3)鈥揌 Arylation
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- 作者：Dominic P. Affron ; Owen A. Davis ; James A. Bull
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：September 19, 2014
- 年：2014
- 卷：16
- 期：18
- 页码：4956-4959
- 全文大小：381K
- ISSN：1523-7052
文摘
Functionalization of C(sp3)鈥揌 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.