Premium
Kinetic Resolution of Amines: A Highly Enantioselective and Chemoselective Acetylating Agent with a Unique Solvent‐Induced Reversal of Stereoselectivity
Author(s) -
Arseniyadis Stellios,
Valleix Alain,
Wagner Alain,
Mioskowski Charles
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200453956
Subject(s) - stereoselectivity , enantioselective synthesis , chemistry , solvent polarity , toluene , solvent , kinetic resolution , combinatorial chemistry , organic chemistry , catalysis
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 (1 S ,2 S )‐ 1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90 % ee ( S ) in DMPU at −20 °C with a 33 % conversion.