Patent ID: 8252941

Claim:
A process of making an enantioenriched α-aminooxyketone comprising reacting a ketone of formula (II): with a nitroso compound of formula (IIIa) or (IIIb): in the presence of a solvent and a catalyst of formula (IVa): wherein: R 1 and R 2 independently represent either hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted aryl group; or R 1 and R 2 together form a cycloalkyl ring; R 3 is each independently selected from the group consisting of: hydrogen, halogen, —OR 5 , —OC(O)R 5 , —CN, —C(O)R 5 , —CO 2 R 5 , —C(O)NR 5 R 5′ , —NO 2 , —NR 5 R 5′ , —NRC(O)R 5 , —NR 5 CO 2 R 5′ , —NR 5 S(O) 2 R 5′ , —SR 5 , —S(O)R 5 , —S(O) 2 R 5 , —S(O) 2 NR 5 R 5′ , C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl; wherein each R 5 and R 5′ may be independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl; n is an integer from 0-5; R 4 is substituted or unsubstituted alkyl; the configuration of the stereogenic carbon alpha to the nitrogen on the pyrolidine ring is the (L) or optionally (D) configuration.