1064689-08-2Relevant academic research and scientific papers
Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: Reversal of the stereochemistry by tuning the 3,3′-disubstituents of phosphoric acids
Li, Nan,Chen, Xiao-Hua,Song, Jin,Luo, Shi-Wei,Fan, Wu,Gong, Liu-Zhu
supporting information; experimental part, p. 15301 - 15310 (2010/01/30)
Organocatalytic enantioselective Biginelli and Biginelli-like reactions by chiral phosphoric acids derived from 3,3′-disubstituted binaphthols have been investigated. The size of 3,3′-substituents of the catalysts is able to control the stereochemistry of
Enantioselective synthesis of SNAP-7941: Chiral dihydropyrimidone inhibitor of MCH1-R
Goss, Jennifer M.,Schaus, Scott E.
supporting information; experimental part, p. 7651 - 7656 (2009/04/11)
(Chemical Equation Presented) An enantioselective synthesis of SNAP-7941, a potent melanin concentrating hormone receptor antagonist, was achieved by using two organocatalytic methods. The first method utilized to synthesize the enantioenriched dihydropyrimidone core was the Cinchona alkaloid-catalyzed Mannich reaction of β-keto esters to acylimines and the second was the chiral phosphoric acid-catalyzed Biginelli reaction. Completion of the synthesis was accomplished via selective urea formation at the N3 position of the dihydropyrimidone with the 3-(4-phenylpiperidin-1-yl)propylamine side chain fragment. The synthesis of SNAP-7921 highlights the utility of asymmetric organocatalytic methods in the construction of an important class of chiral heterocycles.
