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Tunable and Diastereoselective Brønsted Acid Catalyzed Synthesis of β-Enaminones
Ye-Won Kang1, Yu Jin Cho1, Seung Jin Han1
1Department of Energy Systems Research, Ajou University , Suwon 443-749, Korea.
Abstract:
The Brønsted acid catalyzed Meyer-Schuster reaction of hemiaminals was studied for the stereoselective synthesis of β-enaminones. Hemiaminals were formed from propargyl aldehydes (or the oxidation of propargyl alcohols) and amines in the presence of Brønsted acids. A critical step to control the stereochemistry of the products is the protonation of the corresponding allenol intermediate, which is dictated by the Brønsted acid used, the steric effect of the amine, and the electronic effect of the propargyl aldehyde.
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Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...

