137310-16-8Relevant articles and documents
Synthesis of chiral fluorides by sequential organocatalyzed desymmetrization of glutaric anhydrides and photoredox-catalyzed decarboxylic fluorination
Zhao, Jia-Jia,Yu, Shouyun
, p. 391 - 394 (2021)
We have developed an efficient method for the preparation of chiral fluorinated compounds by sequential organocatalyzed desymmetrization of 3-substituted glutaric anhydrides and photoredox-catalyzed decarboxylic fluorination. Chiral fluorides can be prepa
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
supporting information, p. 309 - 317 (2018/02/19)
A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.
Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides
Yan, Lin-Jie,Wang, Hai-Feng,Chen, Wen-Xue,Tao, Yuan,Jin, Kai-Jun,Chen, Fen-Er
, p. 2249 - 2253 (2016/07/19)
The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S,2R)-12 a–f and (1R,2R)-15 a–c, and their use in the enantioselective alcoholysis of meso-anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)-12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)-15 a–c. This technique was used to synthesize (R)-(?)-baclofen.
CINCHONA-BASED BIFUNCTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME
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Page/Page column 22; 27, (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; experimental part, 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.
An efficient synthesis of (R)- and (S)-baclofen via desymmetrization
Ji, Lei,Ma, Yuheng,Li, Jin,Zhang, Liangren,Zhang, Lihe
scheme or table, p. 6166 - 6168 (2009/12/26)
A short and highly enantioselective synthesis of both enantiomers of GABA agonist baclofen in four steps with total yields of 32.8% [for (S)-isomer] and 35.1% [for (R)-isomer] is reported. The key step involved desymmetrization of cyclic anhydride with mo
Enzymatic desymmetrization of 3-arylglutaric acid anhydrides
Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 2475 - 2485 (2007/10/03)
Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.
Chemoenzymatic enantioselective synthesis of baclofen
Chenevert,Desjardins
, p. 2312 - 2317 (2007/10/02)
We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium. We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium.
Chemoenzymatic synthesis of both enantiomers of baclofen
Chenevert, Robert,Desjardins, Michel
, p. 4249 - 4250 (2007/10/02)
Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.
