The N,N′-dioxide/Ni(ii)-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of methyleneindolinones with hetero-substituted alkenes?

Chemical Communications Pub Date: 2015-06-23 DOI: 10.1039/C5CC04245C

Abstract

The highly efficient catalytic asymmetric inverse-electron-demand hetero-Diels–Alder reaction of methyleneindolinones with hetero-substituted alkenes has been accomplished under mild reaction conditions. In the presence of chiral N,N′-dioxide/Ni(II) complexes, a wide range of optically active dihydropyran-fused indoles were obtained in up to 99% yield, >95?:?5 dr and 99% ee.

Graphical abstract: The N,N′-dioxide/Ni(ii)-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of methyleneindolinones with hetero-substituted alkenes
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