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.
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.
Tillman
A Louise
AL
University of Cambridge, Chemical Laboratory, Lensfield Road, Cambridge, UKCB2 1EW.
Ye
Jinxing
J
Dixon
Darren J
DJ
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
D002930:Cinchona Alkaloids; D004952:Esters; D007097:Imines; D007659:Ketones; D008314:Malonates; D008352:Mannich Bases; C030290:malonic acid; C010086:cinchonine