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Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction.
Chirality. 2014 Apr; 26(4):209-13.C

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Qu C
College of Chemistry and Chemical Engineering, Henan University, Kaifeng, China.
Zhao W
No affiliation info available
Zhang L
No affiliation info available
Cui Y
No affiliation info available

MeSH

AldehydesBenzaldehydesBiochemistryCatalysisCyclohexanonesHorseradish PeroxidasePolymerizationProlineStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24619918

Citation

Qu, Chengke, et al. "Preparation of Immobilized L-prolinamide Via Enzymatic Polymerization of Phenolic L-prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction." Chirality, vol. 26, no. 4, 2014, pp. 209-13.
Qu C, Zhao W, Zhang L, et al. Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction. Chirality. 2014;26(4):209-13.
Qu, C., Zhao, W., Zhang, L., & Cui, Y. (2014). Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction. Chirality, 26(4), 209-13. https://doi.org/10.1002/chir.22302
Qu C, et al. Preparation of Immobilized L-prolinamide Via Enzymatic Polymerization of Phenolic L-prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction. Chirality. 2014;26(4):209-13. PubMed PMID: 24619918.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparation of immobilized L-prolinamide via enzymatic polymerization of phenolic L-prolinamide and evaluation of its catalytic performance for direct asymmetric aldol reaction. AU - Qu,Chengke, AU - Zhao,Wenshan, AU - Zhang,Lei, AU - Cui,Yuanchen, Y1 - 2014/03/12/ PY - 2013/10/23/received PY - 2013/12/20/revised PY - 2014/01/08/accepted PY - 2014/3/13/entrez PY - 2014/3/13/pubmed PY - 2015/5/15/medline KW - L-prolinamide KW - asymmetric aldol reaction KW - polymer-supported catalyst KW - polymerization SP - 209 EP - 13 JF - Chirality JO - Chirality VL - 26 IS - 4 N2 - 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. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/24619918/Preparation_of_immobilized_L_prolinamide_via_enzymatic_polymerization_of_phenolic_L_prolinamide_and_evaluation_of_its_catalytic_performance_for_direct_asymmetric_aldol_reaction_ DB - PRIME DP - Unbound Medicine ER -