135865-78-0Relevant articles and documents
Concise enantioselective synthesis of (+)-sertraline and (-)-CP-52002 using proline catalysis
Kalshetti, Rupali,Venkataramasubramanian,Kamble, Sanjay,Sudalai, Arumugam
, p. 1053 - 1055 (2016)
A short enantioselective synthesis of (+)-sertraline and its C4 epimer (-)-CP-52002 with an overall yield of 30%, respectively, as its hydrochloride has been described. The key steps are the proline catalyzed Mannich reaction of acetaldehyde and acid catalyzed intramolecular Friedel-Crafts' alkylation reaction of olefin proceeding with high optical purities.
Chiral Bronsted acid-catalyzed tandem aza-ene type reaction/cyclization cascade for a one-pot entry to enantioenriched piperidines
Terada, Masahiro,Machioka, Kyoko,Sorimachi, Keiichi
, p. 10336 - 10337 (2007)
A chiral monophosphoric acid-catalyzed tandem aza-ene type reaction/cyclization cascade enabled the rapid construction of enantioenriched piperidine derivatives as key structural elements of numerous natural products. The potential of such cascade transformations is highlighted through their ability to achieve a rapid increase in molecular complexity from simple enecarbamates and a broad range of aldimines while also controlling three stereogenic centers in a highly diastereo- and enantioselective manner. Copyright
Asymmetric synthesis method of chiral beta-amino aldehyde compound
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Paragraph 0128-0133, (2020/03/11)
The invention discloses an asymmetric synthesis method of a chiral beta-amino aldehyde compound as shown in a formula (I) which is described in the specification. The asymmetric synthesis is carried out in an organic solvent with imine as shown in a formula (II) and aldehyde as shown in a formula (III) as reactants. The method is characterized in that the reaction is carried out under the action of a supramolecular catalyst constructed by a chiral catalyst and a polymer, wherein the chiral catalyst is one as described in the specification, and the polymer is PEG and/or PPG. According to the invention, PPG/PEG and the chiral catalyst are utilized to construct the supramolecular catalyst for asymmetric synthesis of the chiral beta-amino aldehyde compound, so product yield is significantly improved.
Configurationally Stable (S)- and (R)-α-Methylproline-Derived Ligands for the Direct Chemical Resolution of Free Unprotected β3-Amino Acids
Zhou, Shengbin,Wang, Shuni,Wang, Jiang,Nian, Yong,Peng, Panfeng,Soloshonok, Vadim A.,Liu, Hong
, p. 1821 - 1832 (2018/04/27)
Reported herein is a chemical method for the direct resolution of unprotected racemic β-substituted-β-amino acids (β3-AAs) that uses specially designed, stable, and recyclable α-methylproline-derived chiral ligands. The versatility of this methodology is unmatched by biocatalytic approaches. The method shows a broad synthetic generality for various aryl- or alkyl-substituted β3-AAs, and the new nonracemizable ligands can be accessed readily. Furthermore, the presented method produces an excellent stereochemical outcome and has a fully recyclable source of chirality, and the reaction conditions are operationally simple and convenient. The procedure has also been successfully applied to the scalable synthesis of the anti-HIV drug maraviroc.