Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines
Azusa Kondoh, Rihaku Ojima, Masahiro Terada
Abstract
A ring expansion of 2-benzoylpyrrolidines, which involves the formal fluorinative ring opening utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis and a subsequent intramolecular reductive amination, was developed. The operationally simple three-step protocol provides an efficient access to 2-aryl-3-fluoropiperidines. The methodology was further applied to the syntheses of azepanes and tetrahydroquinolines.
Topics & Concepts
ChemistryRing (chemistry)Intramolecular forceArylCombinatorial chemistryAminationReductive aminationStereochemistryCatalysisOrganic chemistryAlkylFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis