Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: synthesis of cyclic amines with a tertiary fluorine at C3.
As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of the ring expansion of cyclic 2-hydroxymethyl amines induced by diethylaminosulfur trifluoride (DAST) to produce cyclic β-fluoro amines was studied as well as the enantioselectivity of the process.
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Bruno
B
Anxionnat
Benoit
B
Robert
Pascal
P
George
Gino
G
Ricci
Marc-Antoine
MA
Perrin
Domingo
D
Gomez Pardo
Janine
J
Cossy
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry*; D003500:Cyclization; D004048:Diethylamines / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D000605:Amino Alcohols; D004048:Diethylamines; D005461:Fluorine; C040394:diethylaminosulfur trifluoride