synthesis and characterization of some new c2 symmetric chiral bisamide ligands derived from chiral feist’s acid合成和表征的一些新的c2对称的手性双酰胺配体由手性无用的酸.pdfVIP

Molecules 2012, 17, 5550-5563; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Characterization of Some New C Symmetric 2 Chiral Bisamide Ligands Derived from Chiral Feist’s Acid Abdullah M. A. Al Majid *, Mohammad Shahidul Islam *, Zeid Abdullah Al-Othman, Ahlam F. Al-Salhoob and Assem Barakat Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; E-Mails: zaothman@.sa (Z.A.A.-O.); rhofy29@ (A.F.A.-S.); ambarakat@.sa (A.B.) * Authors to whom correspondence should be addressed; E-Mails: amajid@.sa (A.M.A.A.M.); shahid.10amui@ (M.S.I.); Tel.: +9661-467-5889 (A.M.A.A.M.); Fax: +9661-467-5992 (A.M.A.A.M.); Tel.: +9665-467-5884 (M.S.I.); Fax: +9661-467-5992 (M.S.I.). Received: 7 February 2012; in revised form: 16 April 2012 / Accepted: 20 April 2012 / Published: 9 May 2012 Abstract: The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5a-d and (1S,2S)-6a-d were synthesized in quantitative yield from (1R,2R)-(+)-3- methylenecyclo-propane-1,2-dicarboxylic acid (1R,2R)-3 and (1S,2S)-(-)-3-methylene- cyclopropane-1,2-dicarboxylic acid (1S,2S)-3, in two steps, respectively. The chiral Feist’s acids (1R,2R)-3 and (1S,2S)-3 were obtained in good isomeric purity by resolution of trans-(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8