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Photocyclization of enamines to access Spiroindolines and Spirooxindoles in continuous flow

  • Moses Moustakim
  • , Brian Ledford
  • , Jacob A. Garwin
  • , Michael J. Boyd

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

We report an expedited flow chemistry approach to the catalyst/photosensitizer-free UV photocyclizations of aryl-enamines to afford spiroindolines. The photocyclizations occur under mild conditions and are tolerant to a variety of substituted aryl-enamines and spirocycle ring sizes. This flow protocol has a wide substrate scope and addresses the problems of irreproducibility and scalability of batch protocols. The utility of this reaction is demonstrated in a shortened formal synthesis of (±)-horsfiline.

Original languageEnglish
Article number152111
JournalTetrahedron Letters
Volume61
Issue number28
DOIs
StatePublished - 9 Jul 2020
Externally publishedYes

Keywords

  • Flow
  • Photochemistry
  • Spiroindolines
  • Spirooxindoles

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