The catalytic asymmetric ene-type reactions of vinylogous hydrazone were accomplished by using chiral<i> N,N′</i>-dioxide–metal salt complexes as catalysts. A wide range of electrophiles, including isatins, α-ketoester, imines, and aldehydes reacted with (E)-2-methyl-<i>N</i>-(piperidin-1yl)prop-2-en-1-imine efficiently, affording the corresponding homoallylic alcohols and amines in high yields (up to 99%) with excellent ee values (up to 99%). The methodology provided a convenient way to synthesize bioactive chiral α-methylene-γ-butyrolactone derivatives.

Catalytic enantioselective ene-type reactions of vinylogous hydrazone: Construction of α-methylene-γ-butyrolactone derivatives

2019 Fall National Meeting

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