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

作者：Gnanamani Elumalai; Ramanathan Chinnasamy Ramaraj^*

来源：Tetrahedron: Asymmetry , 2009, 20(19): 2211-2215.

DOI：10.1016/j.tetasy.2009.09.011

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 in acetonitrile. 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.

• 出版日期2009-10-6