Kinetic Resolution of Amines: A Highly Enantioselective and Chemoselective Acetylating Agent with a Unique Solvent-Induced Reversal of Stereoselectivity


  • We thank Rhodia for financial support to S.A., as well as Dr. A. De Cian and Dr. N. Gruber for their helpful collaborations in the collection of the X-ray crystallographic data.


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Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereoselectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90 % ee (S) in DMPU at −20 °C with a 33 % conversion.