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

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• 作者：Limin Shi ; Chuangan Tao ; Qin Yang ; Yong Ethan Liu ; Jing Chen ; Jianfeng Chen ; Jiaxin Tian ; Feng Liu ; Bo Li ; Yongling Du ; Baoguo Zhao
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 4, 2015
• 年：2015
• 卷：17
• 期：23
• 页码：5784-5787
• 全文大小：411K
• ISSN：1523-7052

文摘

A series of chiral pyridoxals 8 and 9 have been developed from commercially available pyridoxine and (S)-伪,伪-diarylprolinols. The pyridoxals exhibited good catalytic activity in an asymmetric transamination of 伪-keto acids with 2,2-diphenylglycine (7f) as the amine source to give various 伪-amino acids in 29鈥?5% yields with 53鈥?0% ee鈥檚. 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.