title: Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative.
abstract: A highly enantioselective Mannich reaction between malonate esters and N-Boc and N-Cbz aldimines, catalysed by a bifunctional cinchonine derivative, has been developed; extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nucleophiles allows the formation of adjacent stereocentres, one of which is quaternary, in high relative and absolute stereocontrol.
authors.affiliation: University of Cambridge, Chemical Laboratory, Lensfield Road, Cambridge, UKCB2 1EW.
authors.forename: A Louise
authors.initials: AL
authors.lastname: Tillman
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D004952:Esters; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D008352:Mannich Bases / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D004952:Esters; D007097:Imines; D007659:Ketones; D008314:Malonates; D008352:Mannich Bases; C030290:malonic acid; C010086:cinchonine