Synfacts 2018; 14(09): 0975
DOI: 10.1055/s-0037-1610602
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Carbonyl-Catalyzed Biomimetic Asymmetric Mannich Reaction

Benjamin List
Oleg Grossmann
Chen J. Gong X. Li J. Li Y. Ma J. Hou C. Zhao G. Yuan W. * Zhao B. * Shanghai Normal University and Chengdu Institute of Organic Chemistry, P. R. of China
Carbonyl Catalysis Enables a Biomimetic Asymmetric Mannich Reaction.

Science 2018;
360: 1438-1442
Further Information

Publication History

Publication Date:
20 August 2018 (online)



The Zhao group reports the activation of primary amines by carbonyls. Using an N-quaternized pyridoxal catalyst for the direct asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines, α,β-diamino acid esters were obtained in good yields and excellent stereoselectivities.



Based on their recently developed chiral pyridoxal and pyridoxamine catalysts for transamination reactions (J. Am. Chem. Soc. 2016, 138, 10730), the authors developed a catalyst that activates primary amines through carbonyl catalysis. In contrast to other α-functionalizations of primary amines, this fascinating catalysis strategy does not require protecting-group manipulation.