1088705-55-8Relevant 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.
Discovery of bifunctional thiourea/secondary-amine organocatalysts for the highly stereoselective nitro-Mannich reaction of α-substituted nitroacetates
Han, Bo,Liu, Qing-Ping,Li, Rui,Tian, Xu,Xiong, Xiao-Feng,Deng, Jin-Gen,Chen, Ying-Chun
supporting information; experimental part, p. 8094 - 8097 (2009/09/28)
The readily accessible bifunctional thiourea/secondary-amine organocatalysts for the highly stereoselective Nitro-Mannich reaction of simple esters of α-substituted nitroacids and N-Boc imines were reported. The enantioselectivity of the isomer is found to increase and the N-H group plays a crucial role in the catalytic transition state other than acting as Bronsted base. Good enantioselectivity could be obtained catalyzed by urea-secondary amine and the enantiomeric excess (ee) value is found to decrease in the absence of 4A molecular sieves. In case of methyl 2-nitropropanoiate, excellent diastereo- and enantioselectivities are observed for aryl imines nearing diverse electron-withdrawing or donating substitutions. The nitro-Mannich products resulting from α-phenyl nitroacetate and N-Boc benzaldimine, are found to be labile at ambient temperature due to its crowded structure.