An enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with N-benzoyl imines was demonstrated using a chiral phosphoric acid catalyst. Cycloaddition products having fluorine functionality were formed in high yields with excellent diastereo- and enantioselectivities. Further manipulation of the enantioenriched cycloaddition product with silyl enol ether in the presence of BiCl3 catalyst afforded substitution product with retention of the dihydro-4H-1,3-oxazine framework through selective carbon−fluorine bond cleavage without loss of enantiomeric excess.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry