PAA-supported Hantzsch 1,4-dihydropyridine ester: an efficient catalyst for the hydrogenation of α,β-epoxy ketones

• Published in: Tetrahedron letters Vol. 54; no. 39; pp. 5374 - 5377
• Main Authors: Zhou, Xin-Feng, Wang, Peng-Fei, Geng, Ye, Xu, Hua-Jian
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 25.09.2013; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Hantzsch ester; NADH co-enzyme model; Physical Sciences; Science & Technology; Water-soluble polymer; α,β-Epoxy ketones; β-Hydroxy ketones; NADH co-enzyme model; Water-soluble polymer; β-Hydroxy ketones; α,β-Epoxy ketones; Hantzsch ester; ASYMMETRIC TRANSFER HYDROGENATION; SILICA-GEL; SOLID-PHASE REACTIONS; ALPHA,BETA-UNSATURATED ALDEHYDES; SELECTIVE REDUCTION; NAD(P)H MODEL; p-Hydroxy ketones; ELECTRON-TRANSFER; CHIRAL NADH MODELS; ALPHA-HALO KETONES; DOUBLE-BOND; alpha,beta-Epoxy ketones
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2013.07.112

A new type of water-soluble polymer-supported NADH co-enzyme model-PAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PAA–HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of α,β-epoxy ketones to the corresponding β-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA–HEH was an optimal potential for recycling use.