A binaphthyl sulfonimide organocatalyst was used to promote highly
enantioselective and diastereoselective Michael addition reactions
of ketones to nitroalkenes in water. In most cases, the products
were obtained in good yields with excellent enantioselectivities
and diastereoselectivities (93-97% ee, up to >99:1
dr). The catalyst could also be used in an asymmetric Michael addition of
isobutyraldehyde to nitroalkenes to give the desired products in moderate yields and moderate enantioselectivities
(up to 83% ee).
asymmetric catalysis - organocatalysis - Michael
additions - nitroalkenes - sulfonimides
