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

被引：126

作者：

Affron, Dominic P. ^{[1
]}

Davis, Owen A. ^{[1
]}

Bull, James A. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

ALPHA-AMINO-ACIDS; C-H BONDS; LEAD-ORIENTED SYNTHESIS; INTRAMOLECULAR AMINATION; 3-DIMENSIONAL FRAGMENTS; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; CARBON CENTERS; NITROGEN ATOM; PYRROLIDINE;

D O I：

10.1021/ol502511g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalization of C(sp(3)) 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.

引用

页码：4956 / 4959

页数：4

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