Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts

被引：107

作者：

Bui, Tommy

Hernandez-Torres, Gloria

Milite, Ciro

Barbas, Carlos F., III ^{[1
]}

机构：

[1] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 24期

关键词：

ASYMMETRIC-SYNTHESIS; RECEPTOR ANTAGONIST; ARYLBORONIC ACIDS; CONSTRUCTION; DERIVATIVES; CYANOACETATES; 2-OXINDOLES; ALLYLATION; ALKYLATION; ALDEHYDES;

D O I：

10.1021/ol102493q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective alpha-amination of aryl oxindoles catalyzed by a dimeric quinidine has been developed. The reaction is general, broad in substrate scope, and affords the desired products in good yields with good to excellent enantioselectivities. This study provides the first examples of a general organocatalytic method for the creation of nitrogen-containing, tetrasubstituted chiral centers at C-3 of various aryl oxindoles. Furthermore, new catalysts and insights into structural elements of the catalysts that significantly influence enantioselectivities are disclosed.

引用

页码：5696 / 5699

页数：4

共 66 条

[1]

[Anonymous], 2009, Curr. Bioact. Compd., DOI [10.2174/157340709787580900, DOI 10.2174/157340709787580900]

[2]

Banks R. E., 1994, ORGANOFLUORINE CHEM

[3] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].