4.7 Article

A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

Journal

CHEMICAL COMMUNICATIONS
Volume 50, Issue 88, Pages 13585-13588

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc06683a

Keywords

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Funding

  1. European Research Council [259056]
  2. EPSRC
  3. NSF [CHE-1026826]
  4. Croatian Science Foundation [02.03./158]
  5. EPSRC [EP/I003398/1] Funding Source: UKRI
  6. Engineering and Physical Sciences Research Council [EP/I003398/1, 1242733] Funding Source: researchfish
  7. European Research Council (ERC) [259056] Funding Source: European Research Council (ERC)

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A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.

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