Processes of enantioselectively forming an aminoxy compound and an 1,2-oxazine compound

A process of enantioselectively forming an 1,2-oxazine compound of Formula (13)

• wherein R2 is one of hydrogen, an aliphatic group, and an alicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si,
• R3 is one of hydrogen, halogen, OR6, an aliphatic group with a main chain having 1 to about 10 carbon atoms and 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and
• R8 is one of hydrogen, NO2, CN, C(R40)O, COOR40, and CONR40R41, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si,
• wherein R40 and R41 are independent from one another one of hydrogen, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and
• Z is one of NO2, CN, C(R42)O, COOR42, and CONR42R43, wherein R42 and R43 are independent from one another one of hydrogen, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si,
• the process comprising contacting a carbonyl compound of Formula (11)
• and a nitroso compound of Formula (2)
• in the presence of a chiral catalyst, the catalyst being a compound of Formula (IX)
• wherein R4 and R5 are independently one of COOH and
• Y is one of CHOH, O, S, Se, CH2, CHOH, CHSH and CHSeH,
• thereby forming a reaction mixture, and
• allowing the carbonyl compound of Formula (1) and the nitroso compound of Formula (2) to react in the reaction mixture, thereby allowing the formation of the 1,2-oxazine compound of Formula (13).