Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: synthesis of cyclic amines with a tertiary fluorine at C3.

Bruno Anxionnat, Benoit Robert, Pascal George, Gino Ricci, Marc-Antoine Perrin, Domingo Gomez Pardo, Janine Cossy

Index: J. Org. Chem. 77(14) , 6087-99, (2012)

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Abstract

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.