title: Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction.
abstract: Phenolic L-prolinamide was allowed to participate in enzymatic polymerization with horseradish peroxidase as the catalyst, generating immobilized L-prolinamide. The catalytic performance of the resultant polymer-supported L-prolinamide for direct asymmetric aldol reaction between aromatic aldehyde and cyclohexanone was studied. The results show that as prepared L-prolinamide can catalyze the aldol reaction at room temperature in the presence of H2O. Relevant aldol addition products are obtained with good yields (up to 91%), high diastereoselectivities (up to 6:94 dr), and medium enantioselectivities (up to 87% ee). Moreover, the title polymer-supported catalyst can be recovered and reused for at least five cycles while the activity remains almost unchanged.
authors.affiliation: College of Chemistry and Chemical Engineering, Henan University, Kaifeng, China.
authors.forename: Chengke
authors.initials: C
authors.lastname: Qu
authors.forename: Wenshan
authors.initials: W
authors.lastname: Zhao
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Yuanchen
authors.initials: Y
authors.lastname: Cui
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D001671:Biochemistry / Q000379:methods*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry; D006735:Horseradish Peroxidase / Q000737:chemistry / Q000378:metabolism; D058105:Polymerization; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001547:Benzaldehydes; D003512:Cyclohexanones; C029915:4-nitrobenzaldehyde; C036468:cyclohexanone; C116609:3-hydroxybutanal; D011392:Proline; D006735:Horseradish Peroxidase; C056291:prolinamide
keywords: L-prolinamide; asymmetric aldol reaction; polymer-supported catalyst; polymerization