1120500-32-4Relevant academic research and scientific papers
Novel, Chiral, and Enantiopure C2-Symmetric Thioureas Promote Asymmetric Protio-Pictet-Spengler Reactions by Anion-Binding Catalysis
Retini, Michele,Bartoccini, Francesca,Zappia, Giovanni,Piersanti, Giovanni
supporting information, p. 825 - 829 (2021/02/01)
Although anion-binding processes are well-known for their crucial role in molecular recognition, they have only recently been utilized for catalysis. Herein, a new class of chiral, enantiopure C2-symmetrical thioureas that, in combination with 4-methoxybenzoic acid, promotes the enantioselective protio-Pictet-Spengler reaction to provide unprotected tetrahydro-β-carbolines in good yields (40–93 %) and moderate-to-high enantioselectivities (34–95 % ee) in one step from tryptamine and aldehyde derivatives is described. The formation of a chiral catalyst-anion complex was explored by 1H NMR.
Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction
Klausen, Rebekka S.,Kennedy, C. Rose,Hyde, Alan M.,Jacobsen, Eric N.
supporting information, p. 12299 - 12309 (2017/09/12)
An investigation of the mechanism of benzoic acid/thiourea co-catalysis in the asymmetric Pictet-Spengler reaction is reported. Kinetic, computational, and structure-activity relationship studies provide evidence that rearomatization via deprotonation of
Weak Bronsted acid-thiourea co-catalysis: Enantioselective, catalytic protio-pictet-spengler reactions
Klausen, Rebekka S.,Jacobsen, Eric N.
supporting information; experimental part, p. 887 - 890 (2009/07/25)
The development of one-pot imine formation and asymmetric Pictet-Spengler reactions cocatalyzed by a chiral thiourea and benzoic acid is described. Optically active tetrahydro-β-carbolines, ubiquitous structural motifs in biologically active natural produ
