Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst

A method of cyclizing an alkene, said method comprising:

• contacting an alkene having the formula:
• wherein
• b is selected from 1 and 2;
• R1, R2 and R3 are members independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroraryl, and
• a member selected from R1 and R2, R2 and R3, and R1, R2 and R3, together with the atoms to which they are attached are optionally joined to fowl a ring system;
• and
• R4 is a member selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl,
• with an ion pair having the formula:
• [A]n+[B]n−,
• wherein n is 1
• and A is
• B is a chiral anion having the formula:
• wherein
• R10, R10a, R11, R11a, R12, R12a, R13, R13a are independently members selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, halogen, CN, CF3, acyl, —SO2NR8R9, —NR8R9, —OR8, —S(O)2R8, —C(O)R9, —COOR8, —CONR8R9, —S(O)2OR8, —OC(O)R8, —C(O)NR8R9, —NR8C(O)R9, —NR8SO2R9 and —NO2, wherein two or more of R10, R10a, R11, R11a, R12, R12a, R13, R13a , together with the atoms to which they are bonded, are optionally joined to form a ring system which is a member selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl
• wherein
• R8 and R9 are members independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl, and R8 and R9, together with the atoms to which they are bonded, are optionally joined to form a 5- to 7-membered ring under conditions appropriate to cyclize said alkene.