Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides

We report a highly
regio-, diastereo- and enantioselective vicinal
dihalogenation of allyl amides. E- and Z-alkenes with both aryl and alkyl substituents were compatible with
this chemistry. This is the result of exquisite catalyst controlled
regioselectivity enabling use of electronically unbiased substrates.
The reaction employs commercially available catalysts and halenium
sources along with cheap inorganic halide salts to affect this transformation.
A preliminary effort to extend this chemistry to heterodihalogenation
is also presented.