title: Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines.
abstract: A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99% ee) were obtained for a range of substrates.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK).
authors.forename: Irene
authors.initials: I
authors.lastname: Ortín
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D002384:Catalysis; D003500:Cyclization; D048288:Imidazolines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D048288:Imidazolines; D007097:Imines; D007659:Ketones; D009570:Nitriles; C542835:ketimine
keywords: Mannich reaction; asymmetric catalysis; cooperative catalysis; imidazolines; ketimines