80650-85-7Relevant academic research and scientific papers
Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine
Hu, Xiao-Mu,Zhang, Dong-Xu,Zhang, Sheng-Yong,Wang, Ping-An
, p. 39557 - 39564 (2015/05/20)
A novel series of dipeptide-like organocatalysts derived from proline, amino acids and primary amines have been prepared for direct asymmetric aldol reactions between various aromatic aldehydes and acetone to afford aldol products in good yields (up to 82%) and moderate enantioselectivities (up to 67% ee) with only 1 mol% of catalyst-loading in brine. Under the same conditions, the direct asymmetric aldol reactions of aromatic aldehydes and cyclohexanone give aldol products with high yields (up to 91%) and moderate to good enantioselectivities (up to 88% ee) and excellent diastereoselectivities (up to 99% dr). These organocatalysts are easily synthesized from commercially available materials in multi-gram scale with high modularity in their structural and stereogenic properties.
Organocatalysis of asymmetric aldol reaction in water: Comparison of catalytic properties of (S)-valine and (S)-proline amides
Kucherenko,Siyutkin,Dashkin,Zlotin
, p. 1010 - 1015 (2014/03/21)
(S)-Valine amides containing (S)- or (R)-α-phenylethyl substituents at N1 atom efficiently catalyze asymmetric aldol reactions between cyclic (heterocyclic) ketones and aromatic aldehydes in water, predominantly giving rise to the aldol anti-di
Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4- isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one
Khatik, Gopal L.,Kumar, Varun,Nair, Vipin A.
supporting information; experimental part, p. 2442 - 2445 (2012/07/03)
Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.
