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Gold(I)-Catalyzed, Stereocontrolled Enamide Synthesis from Primary Amides and Propargyl Aldehydes Using a Tandem Strategy

Sang Min Kim, Dabon Lee and Soon Hyeok Hong*

*Center for Nanoparticle Research, Institute for Basic Science (IBS), Gwanak-gu, Seoul 151-742, Republic of Korea, Email: soonhongsnu.ac.kr

S. M. Kim, D. Lee, S. Hyeok Hong, Org. Lett., 2014, 16, 6168-6171.

DOI: 10.1021/ol503055x (free Supporting Information)


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Abstract

A Au(I)-catalyzed tandem amide addition and Meyer-Schuster rearrangement enables the synthesis of enamides from primary amides and propargyl aldehydes. Enamide stereochemistry was controlled simply by changing solvents and adding a catalytic amount of acid.


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Key Words

enaminones


ID: J54-Y2014