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Chiral Pyridoxal-Catalyzed Asymmetric Biomimetic Transamination of α-Keto Acids

Author:
Shi, Limin, Tao, Chuangan, Yang, Qin, Liu, Yong Ethan, Chen, Jing, Chen, Jianfeng, Tian, Jiaxin, Liu, Feng, Li, Bo, Du, Yongling, Zhao, Baoguo
Source:
Organic letters 2015 v.17 no.23 pp. 5784-5787
ISSN:
1523-7052
Subject:
amino acids, biomimetics, catalysts, catalytic activity, chemical structure, enantioselectivity, keto acids, pyridoxal, pyridoxine, transamination
Abstract:
A series of chiral pyridoxals 8 and 9 have been developed from commercially available pyridoxine and (S)-α,α-diarylprolinols. The pyridoxals exhibited good catalytic activity in an asymmetric transamination of α-keto acids with 2,2-diphenylglycine (7f) as the amine source to give various α-amino acids in 29–85% yields with 53–80% ee’s. The current asymmetric transamination has successfully mimicked a complete biological transamination process characterized by two half-transaminations, a small chiral pyridoxal molecule acting as the catalyst, and enantioselective control.
Agid:
5789960