Asymmetric Michael addition of α-cyano acetates to (E)-1,4-diaryl-2-buten-1,4-diones

An organocatalyzed asymmetric Michael addition of α-cyano acetates to (E)-1,4-diaryl-2-buten-1,4-diones was realized. The reactions afforded various enantioenriched α,α-disubstituted α-cyano acetates with good yields (up to 99%), moderate to good diastereoselectivities (up to 13.3:1) and moderate to good enantioselectivities (up to 94% ee). Furthermore, one of the products was subjected to Paal–Knorr cyclization to provide an α-furanyl-α,α-disubstituted α-cyano acetate in good yield with moderate enantioselectivity. Thus an indirect asymmetric α-heteroarylation of α-cyano acetates has been well established.

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