Biocatalytic α‐Oxidation of Cyclic Amines and N‐Methylanilines for the Synthesis of Lactams and Formamides. Issue 6 (15th February 2017)

• Record Type: Journal Article
• Authors: Zheng, Daijun; Zhou, Xiaojian; Cui, Baodong; Han, Wenyong; Wan, Nanwei; Chen, Yongzheng
• Is Part Of: ChemCatChem. Volume 9:Issue 6(2017)
• Page Start: 937
• Page End: 940
• Publication Date: 2017-02-15
• Subjects: amides -- biocatalysis -- lactams -- oxidation -- regioselectivity; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201601703
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: An environmentally friendly method for the synthesis of lactams and formamides through the biocatalytic α‐oxidation of amines was developed by employing Pseudomonas plecoglossicida ZMU‐T04 as a biocatalyst. In this biocatalytic process, the α‐oxidation of cyclic amines and N ‐methylanilines proceeded smoothly to give the corresponding amides in low to high yields. Furthermore, it was demonstrated that synthetic 3, 4‐dihydroquinolin‐2(1 H )‐one could be used as a key precursor of antidepressant bioactive molecules. The mechanism of this biocatalytic α‐oxidation process was investigated by isotope‐ labeling experiments. Abstract : The big [O] : A highly regioselective, environmentally friendly method for the synthesis of amides from amines is developed. With biocatalytic α‐oxidation, various cyclic amines and N ‐methylanilines are oxidized smoothly to give the corresponding amides. Mechanistic studies suggest that the amide oxygen atom of this biocatalytic α‐oxidation process is derived from water.