Chiral synthesis of isoxazolines, isoxazoline compounds, and uses thereof

A process, comprising:

• reacting, in the presence of a base, a compound having the following formula (I):
• with a compound having the following formula (II):
• to produce a compound having the following formula (III):
• wherein at least the carbons marked “*” are chiral;
• wherein R1, R2, R3, R4, and R5 are each independently hydrogen, an alkyl group, a cycloalkyl group, a halo group, an alkenyl group, an alkynyl group, a hydroxy group, an oxo group, a mercapto group, an alkylthio group, an alkoxy group, an aryl group, a heterocyclic group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, an aralkyl group, a heteroaralkyl group, an aralkoxy group, a heteroaralkoxy group, an amino group, an alkylamino group, a dialkylamino group, an amidine group, an amide group, a carbamoyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylaminocarbonyl group, a dialkylamino carbonyl group, an arylcarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, perhaloalkyl group, a perhaloalkoxy group, a perhalocycloalkyl group, a perhaloalkenyl group, a perhaloalkynyl group, a perhaloaryl group, or a perhaloaralkyl group;
• wherein R1 and R2 may be taken together to form a cyclic group;
• wherein R4 and R5 may be taken together to form a cyclic group;
• wherein each group may be optionally and independently straight or branched;
• wherein each group may be optionally and independently substituted by one or more independent substituents;
• and wherein one or more than one atom in each group may be optionally and independently replaced with one or more independent heteroatoms;
• wherein R6, R7, R8, R9, R10, R11, R12, R13, R14, and R15 are each independently hydrogen, an alkyl group, a cycloalkyl group, a halo group, an alkenyl group, an alkynyl group, a hydroxy group, an oxo group, a mercapto group, an alkylthio group, an alkoxy group, an aryl group, a heterocyclic group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, an aralkyl group, a heteroaralkyl group, an aralkoxy group, a heteroaralkoxy group, an amino group, an alkylamino group, a dialkylamino group, an amidine group, an amide group, a carbamoyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylaminocarbonyl group, a dialkylamino carbonyl group, an arylcarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, perhaloalkyl group, a perhaloalkoxy group, a perhalocycloalkyl group, a perhaloalkenyl group, a perhaloalkynyl group, a perhaloaryl group, or a perhaloaralkyl group;
• wherein m is 0 or 1;
• wherein any two of R6, R7, R8, R9, R10, R11, R12, R13, R14, and R15 may be taken together to form a cyclic group;
• wherein each group may be optionally and independently straight or branched;
• wherein each group may be optionally and independently substituted by one or more independent substituents;
• and wherein one or more than one atom in each group may be optionally and independently replaced with one or more independent heteroatoms;
• with the proviso that R14 and R15 are not identical groups;
• wherein each X is independently carbon or nitrogen, wherein when any X is carbon, it comprises a Y substituent, n being an integer of from 1 to 4 and being the number of X's that are carbon;
• wherein each Y is independently a carbonyl group, a carboxylic acid group, a carboxylate group, hydrogen, an alkyl group, a cycloalkyl group, a halo group, an alkenyl group, an alkynyl group, a hydroxy group, an oxo group, a mercapto group, an alkylthio group, an alkoxy group, an aryl group, a heterocyclic group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, an aralkyl group, a heteroaralkyl group, an aralkoxy group, a heteroaralkoxy group, an amino group, an alkylamino group, a dialkylamino group, an amidine group, an amide group, a carbamoyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylaminocarbonyl group, a dialkylamino carbonyl group, an arylcarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, perhaloalkyl group, a perhaloalkoxy group, a perhalocycloalkyl group, a perhaloalkenyl group, a perhaloalkynyl group, a perhaloaryl group, or a perhaloaralkyl group;
• wherein two Y groups may be taken together to form a cyclic or aryl group;
• wherein each group may be optionally and independently straight or branched;
• wherein each group may be optionally and independently substituted by one or more independent substituents;
• and wherein one or more than one atom in each group may be optionally and independently replaced with one or more independent heteroatoms;
• and
• wherein Z is iodine, bromine, chlorine, alkoxy group, aryloxy group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkylsulfonyloxy group, or alkoxysulfonyloxy group, arylcarbonyloxy group, aryloxycarbonyloxy group, arylsulfonyloxy group, or aryloxysulfonyloxy group.