Highly diastereo- and enantioselective C2 addition of 5H-oxazol-4-ones to γ-keto-α,β-unsaturated esters

The direct C2-addition of 5H-oxazol-4-ones to γ-keto-α,β-unsaturated esters catalyzed by a chiral squaramide has been achieved. Diverse highly functionalized γ-keto esters bearing a C2-oxazolone at the α-position were afforded in high yields with excellent stereoselectivities (d.r. > 20 : 1 and up to 98% ee).