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
Key words
carbonyl catalysis - Mannich reaction - pyridoxal - α,β-diamino acid esters
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.
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.
