The attempted stereoselective synthesis of chiral 2,2′-biindoline

Mary J. Gresser, Steven M. Wales, Paul A. Keller

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

Abstract

The attempted first stereoselective synthesis of 2,2′-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics.

Original languageEnglish
Pages (from-to)6965-6976
Number of pages12
JournalTetrahedron
Volume66
Issue number34
DOIs
Publication statusPublished - 21 Aug 2010

Keywords

  • Biindoline
  • Chiral biamines
  • Helical chiral ligands
  • Metathesis
  • Sharpless AD

Fingerprint Dive into the research topics of 'The attempted stereoselective synthesis of chiral 2,2′-biindoline'. Together they form a unique fingerprint.

Cite this