A Catalytic and Mechanistic Investigation of Optically Active Helical Poly[3-(9-alkylfluoren-9-yl)propylene oxide]s in the Enantioselective Addition of Ethylmagnesium Bromide to Aldehydes

2014 ◽  
Vol 43 (4) ◽  
pp. 462-464 ◽  
Author(s):  
Anlin Zhang ◽  
Nianfa Yang ◽  
Liwen Yang ◽  
Dan Peng
Keyword(s):  
Propylene Oxide ◽  
Optically Active ◽  
Ethylmagnesium Bromide ◽  
Mechanistic Investigation ◽  
Enantioselective Addition

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

Synlett ◽  
2019 ◽  
Vol 30 (14) ◽  
pp. 1693-1697
Author(s):  
Diao Chen ◽  
Jian-Guo Liu ◽  
Xu Zhang ◽  
Ming-Hua Xu
Keyword(s):  
Catalytic System ◽  
Mandelic Acid ◽  
Optically Active ◽  
Antiplatelet Drug ◽  
Reaction Conditions ◽  
Formal Synthesis ◽  
Arylboronic Acids ◽  
Synthetic Utility ◽  
Enantioselective Addition ◽  
Acid Esters

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

scholarly journals Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

2013 ◽  
Vol 9 ◽  
pp. 516-525 ◽  
Author(s):  
Paweł Borowiecki ◽  
Małgorzata Milner-Krawczyk ◽  
Jan Plenkiewicz
Keyword(s):  
Ionic Liquids ◽  
Vinyl Acetate ◽  
Propylene Oxide ◽  
Ring Opening ◽  
Biological Evaluation ◽  
Optically Active ◽  
Chemoenzymatic Synthesis ◽  
Alkyl Bromides ◽  
Wide Range ◽  
Synthesis And Biological Evaluation

Racemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.

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