479423-21-7Relevant articles and documents
Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts
Li, De Run,He, Anyu,Falck
supporting information; experimental part, p. 1756 - 1759 (2010/10/04)
Prochiral ketones are reduced to enantioenriched, secondary alcohols using catecholborane and a family of air-stable, bifunctional thiourea-amine organocatalysts. Asymmetric induction is proposed to arise from the in situ complexation between the borane and chiral thiourea-amine organocatalyst resulting in a stereochemically biased boronate-amine complex. The hydride in the complex is endowed with enhanced nucleophilicity while the thiourea concomitantly embraces and activates the carbonyl.
Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
Puglisi, Alessandra,Benaglia, Maurizio,Annunziata, Rita,Rossi, Davide
experimental part, p. 2258 - 2264 (2009/04/04)
A new and easy synthesis of chiral bifunctional organic catalysts obtained by the combination of (S)-t-leucine-derivatives with (1R,2R)-trans-1,2-diamino-cyclohexane was developed. A few compounds, representatives of a class of organocatalysts containing a thiourea group and a tertiary amino group connected through a chiral backbone, have been successfully synthesized. The catalytic behaviour of such bifunctional chiral molecules, either neutral or protonated species, was investigated in the addition of acetylacetone to β-nitrostyrene as a model reaction. Using the best conditions, high yields and enantioselectivities of up to 85% were obtained. The same metal free catalysts were then employed in the addition of activated nucleophiles to imines: in the reaction of 1,3-diketones with N-CBz imines, the products were isolated in up to 61% ee, while in the reaction with diethyl malonate enantioselectivities up to 71% were reached.
Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: Enantioselective synthesis of β-aryl-β-amino acids
Wenzel, Anna G.,Jacobsen, Eric N.
, p. 12964 - 12965 (2007/10/03)
Highly enantioselective addition reactions between silyl ketene acetals and N-Boc aldimines are catalyzed by the thiourea-based catalyst 1c. Extraordinary scope is observed in this methodology with regard to the imine substrate, with aryl and heteroaromatic derivatives generally affording nearly quantitative yields of β-amino ester product in up to 98% enantioselectivity. Copyright