1239955-60-2Relevant academic research and scientific papers
Cooperative activation of alkyne and thioamide functionalities; Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides
Yazaki, Ryo,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information; experimental part, p. 1778 - 1790 (2012/02/02)
A detailed study of the direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides is described. A soft Lewis acid/hard Bronsted base cooperative catalyst, comprising [Cu(CH3CN)4]PF6,
Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides
Yazaki, Ryo,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information; scheme or table, p. 10275 - 10277 (2010/09/05)
Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Bronsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the β-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate copper thioamide enolate can work as Bronsted base to drive the catalytic cycle via proton transfer. The divergent transformation of the thioamide functionality highlights the synthetic utility of the alkynylation products.
