Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.
ASJC Scopus subject areas
- Organic Chemistry
- Inorganic Chemistry
- Physical and Theoretical Chemistry