Issue 16, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Haz 2018
Accepted
05 Tem 2018
First published
06 Tem 2018

Org. Chem. Front., 2018,5, 2505-2509

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, 5, 2505 DOI: 10.1039/C8QO00545A

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