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Stellios Arseniyadis, Alain Valleix, Alain Wagner and Charles Mioskowski Kinetic Resolution of Amines: A Highly Enantioselective and Chemoselective Acetylating Agent with a Unique Solvent-Induced Reversal of Stereoselectivity Angewandte Chemie International Edition 43

Version of Record online: 16 JUN 2004 | DOI: 10.1002/anie.200453956

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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.

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