Cooperative Brønsted acid-type organocatalysis: alcoholysis of styrene oxides.
We present a mild and efficient method for the completely regioselective alcoholysis of styrene oxides utilizing a cooperative Brønsted acid-type organocatalytic system comprised of mandelic acid (1 mol %) and N,N'-bis-[3,5-bis-(trifluoromethyl)phenyl]-thiourea (1 mol %). Various styrene oxides are readily transformed into their corresponding beta-alkoxy alcohols in good to excellent yields at full conversion. Simple aliphatic and sterically demanding, as well as unsaturated and acid-sensitive alcohols can be employed.
Weil
Torsten
T
Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, Giessen, Germany.
Kotke
Mike
M
Kleiner
Christian M
CM
Schreiner
Peter R
PR