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Title: Design, synthesis, resolution, and stereochemical assignment of a conformationally rigid chiral ligand derived from anthracene and a dienophile containing a pyridine moiety
Authors: Gnanamani, Elumalai
Ramanathan C.R.
Published in: Tetrahedron Asymmetry
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 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. © 2009 Elsevier Ltd. All rights reserved.
Citation: Tetrahedron Asymmetry (2009), 20(19): 2211-2215
Issue Date: 2009
ISSN: 9574166
Author Scopus IDs: 35319775800
Author Affiliations: Gnanamani, E., Department of Chemistry, Pondicherry University, Puducherry, 605 014, India
Ramanathan, C.R., Department of Chemistry, Pondicherry University, Puducherry, 605 014, India
Funding Details: This research work was funded by the Department of Science and Technology, Government of India , New Delhi (Grant No. SR/FTP/CS-04/2006 ). E.G. thanks UGC, New Delhi, for UGC-SAP meritorious scholarship. We thank CIF, Pondicherry University, for NMR facility. X-ray analysis was carried out at National single crystal X-ray facility, School of Chemistry, University of Hyderabad, Hyderabad and SAIF, IIT-Madras, Chennai.
Corresponding Author: Ramanathan, C.R.; Department of Chemistry, Pondicherry University, Puducherry, 605 014, India; email:
Appears in Collections:Journal Publications [CY]

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