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The attempted stereoselective synthesis of chiral 2,2 '-biindoline
Faculty of Science - Papers (Archive)
  • Mary Gresser, University of Wollongong
  • Steven Wales, University of Wollongong
  • Paul A. Keller, University of Wollongong
RIS ID
33868
Publication Date
1-1-2010
Publication Details

Gresser, M. J., Wales, S. M. & Keller, P. A. (2010). The attempted stereoselective synthesis of chiral 2,2 '-biindoline. Tetrahedron, 66 (34), 6965-6976.

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.
Citation Information
Mary Gresser, Steven Wales and Paul A. Keller. "The attempted stereoselective synthesis of chiral 2,2 '-biindoline" (2010)
Available at: http://works.bepress.com/pkeller/34/