Synfacts 2018; 14(09): 0975
DOI: 10.1055/s-0037-1610602
DOI: 10.1055/s-0037-1610602
Organo- and Biocatalysis
Carbonyl-Catalyzed Biomimetic Asymmetric Mannich Reaction
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
Carbonyl Catalysis Enables a Biomimetic Asymmetric Mannich Reaction.
Science 2018;
360: 1438-1442
Further Information
Publication History
Publication Date:
20 August 2018 (online)
Significance
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.
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Comment
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.
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