1207950-21-7Relevant articles and documents
CINCHONA-BASED BIFUNCTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME
-
Page/Page column 22, (2011/09/20)
The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using bifunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.
Chirality holds the key for potent inhibition of the botulinum neurotoxin serotype a protease
Stowe, G. Neil,Silhar, Peter,Hixon, Mark S.,Silvaggi, Nicholas R.,Allen, Karen N.,Moe, Scott T.,Jacobson, Alan R.,Barbieri, Joseph T.,Janda, Kim D.
supporting information; experimental part, p. 756 - 759 (2010/04/05)
(Chemical Equetion Presentation) Botulinum neurotoxin serotype A (BoNT/A) is the most toxic protein known to man and also a bioterrorism agent. As defined by our previous research targeting the etiological agent responsible for BoNT/A intoxication, a protease, we now report on the asymmetric synthesis of four new BoNT/A inhibitors; the most potent of this series is roughly 2-fold more active than the best small molecule inhibitor currently known.
Enantioselective alcoholysis of meso-glutaric anhydrides catalyzed by Cinchona-based sulfonamide catalysts
Park, Sang Eun,Nam, Eun Hye,Jang, Hyeong Bin,Oh, Joong Suk,Some, Surajit,Lee, Yong Seop,Song, Choong Eui
supporting information; scheme or table, p. 2211 - 2217 (2010/11/19)
The bifunctional Cinchona-based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meioglutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X-ray analysis confirmed that these bifunctional organocatalysts 3 do not form Hbonded self-aggregates in both solution and solid state. The synthetic utility of this methodology was also demonstrated in the synthesis of pharmaceutically important γ-amino acids, such as (S)-pregabalin. Of the many asymmetric syntheses of enantiomerically pure (S)-pregabalin reported to date, our synthesis requires the least number of and the simplest steps.