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Significance: The asymmetric formation of allcarbon quaternary stereocenters in an efficient and atom economical manner has been of interest for decades. Trost and co-workers are able to display a highly asymmetric Mannich reaction forming β-amino ketones bearing a quaternary carbon stereocenter, utilizing the Zn-ProPhenol catalytic system previously prepared in the group. Comment: The zinc-catalyzed Mannich reaction forming β-amino ketones proceeded in excellent yield, diastereoand enantioselctivity. The reaction tolerated a wide range of functional groups including heteroaromatics, seven-membered rings, and sterically encumbered imines. The two-point binding of the Boc-imine to the catalyst, as seen in the proposed transition state, explains the stereochemical outcome of the reaction. Selected examples: OH N N Ph HO Ph Ph OH Ph

Zinc-Catalyzed Asymmetric Mannich Reaction Forming β-Amino Ketones