Enantioselective Au(I)-Catalyzed Multicomponent Annulations via Tethered Counterion-Directed Catalysis

Gold(I) complexes of a chiral phosphoric acid-functionalized phosphine the CPA-Phos series enable enantioselective multicomponent reactions between aldehydes, hydroxylamines and cyclic yne-enones, leading to 3,4-dihydro-1H-furo[3,4-d][1,2]oxazines. This represents rare example highly reaction in gold(I) catalysis. The proceed at low catalyst loading provide high yields, total diastereoselectivity, enantiomeric excesses up 99%. Silver-free conditions can be applied. method has very broad scope as it applies both aliphatic aromatic aldehydes hydroxylamines, variety yne-enone-derived oximes. DFT calculations complement this study enlighten reactivity issues mechanistic pathways.