Catalytic C-CN activation and asymmetric cyanoamidation of alkenes: Total syntheses of (+)-horsfiline, (-)-coerulescine, and (-)-esermethole

Venkata Jaganmohan Reddy, Christopher J. Douglas

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19 Scopus citations

Abstract

The detailed study of Pd-catalyzed asymmetric cyanoamidation is reported. Excellent enantioselectivities are attributed to a chiral phosphosphoramidite ligand synthesized in one step from the commercially available materials. Cyanoamidation substrates are easy to prepare from the corresponding anilines. The 3,3-disubstituted oxindole products bear all-carbon quaternary stereocenters and contain a nitrile and an amide, which are valuable functional handles for the synthesis of many indole-containing natural products. Cyanoamidation tolerates free N-H groups, as demonstrated by the successful use of cyanoamidation in the syntheses of (+)-horsfiline and (-)-coerulescine.

Original languageEnglish (US)
Pages (from-to)4719-4729
Number of pages11
JournalTetrahedron
Volume66
Issue number26
DOIs
StatePublished - Jun 26 2010

Bibliographical note

Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.

Keywords

  • Alkaloids
  • Asymmetric catalysis
  • C-C bond activation
  • Total synthesis

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