elumalai gnanamani - Design, synthesis, resolution, and stereochemical assignment of a conformationally rigid chiral ligand derived from anthracene and a dienophile containing a pyridine moiety

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  Publication Details (including relevant citation   information):

  Elumalai Gnanamania  and Chinnasamy Ramaraj Ramanathan

  Tetrahedron: Asymmetry
    Volume 20, Issue 19, 6 October 2009, Pages 2211-2215,

  Abstract:

  The conformationally rigid chiral ligand,   trans-12-(pyridin-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic   acid ethyl ester, 1, was designed and   synthesized in racemic form. Both isomers were successfully   obtained in enantiomerically pure form through classical   resolution using l-(+)-tartaric acid inacetonitrile. The   nature of the diastereomeric complex formed in this resolution   was elucidated using single crystal X-ray crystallographic   studies. The absolute configuration of (+)-1 was   unambiguously assigned as (11S,12S) by single   crystal structural analysis of salt 5 formed   from (+)-1 and l-(+)-tartaric acid.

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