A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction.
A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Filippo
F
Sladojevich
Andrea
A
Trabocchi
Antonio
A
Guarna
Darren J
DJ
Dixon
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry*; D002384:Catalysis; D010720:Phosphines / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000085:Acetates; D000447:Aldehydes; D000470:Alkaloids; D010720:Phosphines; D012834:Silver; C044646:phosphine