1438415-84-9Relevant academic research and scientific papers
Chiral primary amine tagged to ionic group as reusable organocatalyst for asymmetric Michael reactions of C-nucleophiles with α,β-unsaturated ketones
Kucherenko, Alexander S.,Siyutkin, Dmitry E.,Nigmatov, Albert G.,Chizhov, Alexander O.,Zlotin, Sergei G.
supporting information, p. 3078 - 3086 (2013/01/15)
The first primary amine-derived organocatalyst modified with an ionic group for asymmetric Michael reactions of C-nucleophiles with α,β- unsaturated ketones was synthesized. In the presence of this catalyst and an acidic co-catalyst (AcOH), hydroxycoumarin and its sulfur-containing analogue reacted with benzylideneacetone derivatives or cyclohexenone to afford the corresponding Michael adducts in high yields (up to 97%) and with reasonable enantioselectivity (up to 80%). The catalyst could be easily recovered and efficiently reused three times, afterwards, its activity and stereodifferentiating ability gradually declined. The analysis of recovered catalyst samples by ESI-MS allowed us to detect undesirable side reactions that poisoned the catalyst, and propose an approach for its reactivation. Copyright
