title: Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives.
abstract: A highly stereoselective route to functionalized pyrrolidines by the metal-catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction.
authors: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors: Simon M
authors: SM
authors: Nicolle
authors: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors: William
authors: W
authors: Lewis
authors: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors: Christopher J
authors: CJ
authors: Hayes
authors: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK. c.j.moody@nottingham.ac.uk.
authors: Christopher J
authors: CJ
authors: Moody
keywords: aldol reaction; carbenes; diazo compounds; nitrogen heterocycles; transition-metal catalysis