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Asymmetric aldol reaction catalyzed by amino acid tetrapeptides (l-Pro-l-Pro-l-Phe-l-Phe-OMe)†
Yaodong Wang,Yudan Wang,Kexiao Sang,Toshifumi Satoh
Reaction Chemistry & Engineering Pub Date : 04/21/2023 00:00:00 , DOI:10.1039/D3RE00119A
Abstract

Metal-free catalysts have become one of the important research directions in catalysis due to increasing heavy metal pollution. In this paper, the synthesized aromatic amino acid dipeptide (L-Phe-L-Phe-OMe) was connected with a proline dipeptide (L-Pro-L-Pro) by solid phase synthesis reaction to produce the heterogeneous catalyst L-Pro-L-Pro-L-Phe-L-Phe-OMe. The structure of this catalyst was characterized by means of SEM, XRD, and NMR and FTIR spectroscopy. X-ray diffractometry revealed that L-Pro-L-Pro-L-Phe-L-Phe-OMe has a rod crystal structure. Moreover, L-Pro-L-Pro-L-Phe-L-Phe-OMe showed better catalytic activity than a homogeneous small molecule catalyst (high enantioselectivity, ee > 97%) in heterogeneous asymmetric aldol reactions and had good recyclability.

Graphical abstract: Asymmetric aldol reaction catalyzed by amino acid tetrapeptides (l-Pro-l-Pro-l-Phe-l-Phe-OMe)
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