178153-56-5Relevant academic research and scientific papers
Construction of Stereogenic α,α-Disubstituted Cycloalkanones via 1° Amine Thiourea Dual Catalysis: Experimental Scope and Computational Analyses
Kang, Jun Yong,Johnston, Ryne C.,Snyder, Kevin M.,Cheong, Paul Ha-Yeon,Carter, Rich G.
, p. 3629 - 3637 (2016/05/24)
The mechanistic exploration and an expanded experimental discussion of the organocatalyzed, asymmetric Pfau-dAngelo reaction by exploiting a bifunctional 1° amine thiourea catalyst system is disclosed. Notable breadth in substrate scope has been demonstrated on both the cyclic ketone moiety and the α,β-unsaturated electrophile. Exploration into the matched and mismatched selectivity of this process with a ketone containing pre-existing stereocenters has been demonstrated. Computational analyses of the reaction mechanism are reported. In concert with kinetic isotope effect (KIE) experiments, these computational results provide a detailed understanding of the likely mechanism, including the aspects of the organocatalyst scaffold that are critical for stereoselectivity.
Primary amine, thiourea-based dual catalysis motif for synthesis of stereogenic, all-carbon quaternary center-containing cycloalkanones
Kang, Jun Yong,Carter, Rich G.
supporting information; experimental part, p. 3178 - 3181 (2012/08/07)
The enantioselective synthesis of α,α-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic c
