119th General Meeting of the KCS

Type Symposium
Area [SRC 심포지엄] New Trends and Developments in Organic Synthesis
Room No. 303호
Time WED 15:00-:
Code KCS5-4
Subject Selective N-Sulfonyl Enaminone Synthesis from Sulfonamides and Ynones by Controlling the Nature of Au(I) and Au(III) Catalysis
Authors 이다본, 홍순혁*
서울대학교 화학부, Korea
Abstract N-Sulfonyl enaminones are widely utilized synthetic precursors in chemistry and biology. However, previous syntheses have significant limitations mainly on preparing starting materials and controlling selectivity among several possible isomers. Herein, we report a novel and practical method for the synthesis of N-sulfonyl enaminones from easily accessible substrates, sulfonamides and ynones. This method affords two different regioisomers of N-sulfonyl enaminones via chemoselective nucleophilic addition controlled by different catalytic systems taking advantage of the different natures of gold(III) and gold(I) catalysts. The desired regioisomers were obtained selectively by modulating catalytic systems. Moderate to excellent yields and selectivity were achieved with wide range of substrates.
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