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Highly enantioselective desymmetrization of prochiral cyclic α,α-dicyanoalkenes via the direct vinylogous Michael/cyclization domino reaction

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Abstract

The catalytic desymmetric direct vinylogous Michael/cyclization domino reaction of 2-(4-substituted-cyclohexylidene) malononitriles with N-protected methyleneindolinones was realized by a combination of a chiral N,N′-dioxide/Mg(II) complex and an organic base. It provided efficient access to spiroindolinones bearing three adjacent stereogenic centers and a tertiary carbon center at remote sites in high yields, and with excellent dr and ee values.

Graphical abstract: Highly enantioselective desymmetrization of prochiral cyclic α,α-dicyanoalkenes via the direct vinylogous Michael/cyclization domino reaction

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Publication details

The article was received on 01 Jun 2018, accepted on 05 Jul 2018 and first published on 06 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00545A
Citation: Org. Chem. Front., 2018, Advance Article
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    Highly enantioselective desymmetrization of prochiral cyclic α,α-dicyanoalkenes via the direct vinylogous Michael/cyclization domino reaction

    H. Mei, L. Lin, B. Shen, X. Liu and X. Feng, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00545A

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