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Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Science 29 Jun 2018:
Vol. 360, Issue 6396, pp. 1438-1442
DOI: 10.1126/science.aat4210

http://science.sciencemag.org/content/360/6396/1438

发布日期:2018/7/4 发布者:网站管理员 点击数:23【打印