Asymmetric Synthesis of Chiral Sulfoximines via the S-Arylation of Sulfinamides

被引:96
作者
Aota, Yusuke [1 ]
Kano, Taichi [1 ]
Maruoka, Keiji [1 ,2 ,3 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Lab Organocatalyst Chem, Sakyo Ku, Kyoto 6068502, Japan
[3] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China
基金
日本学术振兴会;
关键词
RHODIUM-CATALYZED IMINATION; DIARYLIODONIUM SALTS; ENANTIOSELECTIVE SYNTHESIS; ENANTIOPURE SULFINAMIDES; KINETIC RESOLUTION; NITRENE TRANSFER; NH-SULFOXIMINES; CDK INHIBITOR; BAY; 1000394; SULFOXIDES;
D O I
10.1021/jacs.9b11298
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically active sulfoximines are a promising substance in medicinal chemistry. However, a methodology for preparing chiral sulfoximines in a stereoselective manner has been underdeveloped. Here, we report an asymmetric synthesis of chiral sulfoximines having an aryl group by the newly developed sulfur-selective arylation of easily accessible chiral sulfinamides. The utility of the present method is demonstrated by the asymmetric synthesis of a key intermediate of a COX-2 inhibitor.
引用
收藏
页码:19263 / 19268
页数:6
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