Organocatalysis has provided a revolution in modern catalysis and much effort has been devoted to invent novel reactivities and reactions and/or improve on past results. Amino acids have �re-attracted� the attention, since they are considered a vast chiral pool for fishing new catalysts. Along these lines, examples from our research will be presented where amino acids have been employed either as catalysts, for example the use of beta-phenylalanine for the Michael reaction between a,a-disubstituted aldehydes and maleimides leading to an one-pot synthesis of chiral lactones,1 or as starting material for the synthesis of catalysts, like pyrrolidine-thioxotetrahydropyrimidinone that has been employed successfully in a tandem Michael-Henry reaction.2 Furthermore, research on organocatalysis has not been so actively involved in oxidations. In an effort to provide general protocols for organic oxidations that can be implemented in a wide spectrum of chemical processes embracing the principles of Green Chemistry, we have identified activated ketones, namely perfluoroalkyl ketones, as organocatalysts for various oxidations. Two examples constitute the first organocatalytic oxidation of silanes to silanols3 and the oxidation of tertiary amines and azines to the N-oxides.4[1] Kokotos, C. G. Org. Lett. 2013  , 15, 2406-2409.[2] Tsakos, M.; Elsegood, M. R. J.; Kokotos, C. G. Chem. Commun. 2013  ,49, 2219-2221.[3] Limnios, D.; Kokotos, C. G. ACS Catal. 2013  ,3, 2239-2243.[4] Limnios, D.; Kokotos, C. G. Chem. Eur. J., 2014  ,20, 559-563.

Amino acids, their derivatives and activated ketones: Organocatalysts for asymmetric transformations and green oxidations

248th National Meeting (2014)

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