336105-29-4Relevant articles and documents
Crystal structures of reversible ketone-Based inhibitors of the cysteine protease cruzain
Huang, Lily,Brinen, Linda S.,Ellman, Jonathan A.
, p. 21 - 29 (2003)
The crystal structures of two hydroxymethyl ketone inhibitors complexed to the cysteine protease cruzain have been determined at 1.1 and 1.2 A resolution, respectively. These high resolution crystal structures provide the first structures of non-covalent inhibitors bound to cruzain. A series of compounds were prepared and tested based upon the structures providing further insight into the key binding interactions.
Stereoselective Coupling of N-tert-Butanesulfinyl Aldimines and β-Keto Acids: Access to β-Amino Ketones
Lahosa, Alejandro,Soler, Tatiana,Arrieta, Ana,Cossío, Fernando P.,Foubelo, Francisco,Yus, Miguel
, p. 7481 - 7491 (2017/07/26)
The reaction of chiral N-tert-butanesulfinyl aldimines with β-keto acids under basic conditions at room temperature proceeds with high levels of diastereocontrol, leading to β-amino ketones in high yields. Based on DFT calculations, an eight-membered cyclic transition state involving coordination of the lithium atom to the oxygens of carboxylate and sulfinyl units was proposed, being in agreement with the observed experimental diastereomeric ratios. The synthesis of the piperidine alkaloid (-)-pelletierine was successfully undertaken in order to demonstrate the utility of this methodology.
Influence of HMPA on the stereochemical outcome of the addition of a racemic allenylzinc onto enantiopure N-terf-butanesulfinimines: Stereoselective access to enantiopure cis-ethynylaziridines
Ferreira, Franck,Audouin, Max,Chemla, Fabrice
, p. 5269 - 5278 (2007/10/03)
In the presence of 60 equivalents of HMPA, the condensation of the racemic allenylzinc derived from l -chloro-3-trimethylsilylpropyne onto enantiopure non-a-branched N-tert-butanesulfinimines was proven to give access to the corresponding cis-ethyny-lazir
