Journal article
The attempted stereoselective synthesis of chiral 2,2 '-biindoline
Tetrahedron, Vol.66(34), pp.6965-6976
2010
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.
Details
- Title
- The attempted stereoselective synthesis of chiral 2,2 '-biindoline
- Authors
- Mary J. Gresser (Author) - University of WollongongSteven M. Wales (Author) - University of WollongongPaul A. Keller (Author) - University of Wollongong
- Publication details
- Tetrahedron, Vol.66(34), pp.6965-6976
- Publisher
- Elsevier Ltd.
- DOI
- 10.1016/j.tet.2010.06.035
- ISSN
- 1464-5416
- Organisation Unit
- Student Services and Engagement; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99707484002621
- Output Type
- Journal article
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- Chemistry, Organic
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