The attempted stereoselective synthesis of chiral 2,2 '-biindolineFaculty of Science - Papers (Archive)
AbstractThe 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 InformationMary 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/