Asymmetric Brønsted Acid Catalyzed Synthesis of Triarylmethanes - Construction of Communesin and Spiroindoline Scaffolds

Hsuan Hung Liao, Adisak Chatupheeraphat, Chien Chi Hsiao, Iuliana Atodiresei, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

Abstract

Aza-ortho-quinone methides allow the straightforward asymmetric synthesis of natural-product-inspired indole scaffolds possessing a quaternary stereocenter. Our approach provides access to diverse communesin and spiroindoline derivatives with high enantioselectivity under mild reaction conditions. Predictable substitution patterns are found to be the key to our regiodivergent protocols. Two protocols have been developed for the regiodivergent, asymmetric Brønsted acid catalyzed addition of indoles to in situ generated aza-ortho-quinone methides. Furthermore, a new addition spirocyclization sequence leads, depending on the indole derivative, to communesin and spiroindoline cores with quaternary stereocenters.

Original languageEnglish (US)
Pages (from-to)15540-15544
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number51
DOIs
StatePublished - Dec 14 2015

Keywords

  • Michael addition
  • counterions
  • fluorine
  • organocatalysis
  • rearrangements

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Asymmetric Brønsted Acid Catalyzed Synthesis of Triarylmethanes - Construction of Communesin and Spiroindoline Scaffolds'. Together they form a unique fingerprint.

Cite this