dc.contributor.authorYap, Jeanette See Leng
dc.contributor.authorChen, Houguang Jeremy
dc.contributor.authorLi, Yongxin
dc.contributor.authorPullarkat, Sumod A.
dc.contributor.authorLeung, Pak-Hing
dc.identifier.citationYap, J. S. L., Chen, H. J., Li, Y., Pullarkat, S. A., & Leung, P.-H. (2014). Synthesis, optical resolution, and stereochemical properties of a rationally designed chiral C–N palladacycle. Organometallics, 33(4), 930-940.en_US
dc.description.abstractA novel racemic tertiary amine, 1-(2,5-diisopropylphenyl)-N,N-dimethylethanamine, was synthesized from 2,5-diisopropylbenzaldehyde via a multistep approach in high overall yield. The ortho palladation of this ligand was found to be sensitive to the reaction conditions and the palladating reagents employed. The metal complexation process could thus generate a cyclopalladated complex in high yield, lead to an unexpected N-demethylated amine palladium(II) complex, or both. Both products have been isolated and characterized crystallographically in the solid state and spectroscopically in solution. The racemic cyclopalladated complex could be efficiently resolved via the formation of (S)-prolinato derivatives. The absolute stereochemistries of the resolved diastereomeric complexes were determined by single-crystal X-ray crystallography in the solid state and by 1H–1H rotating frame Overhauser effect (ROESY) NMR spectroscopy in solution. An evaluation of the sterically hindered resolved cyclopalladated units as chiral auxiliaries was conducted in the endo-cycloaddition reaction between 3,4-dimethyl-1-phenylphosphole (DMPP) and ethyl vinyl ketone. The two expected phosphanorbornene adducts were generated with moderate stereoselectivity.en_US
dc.format.extent10 p.en_US
dc.rights© 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organometallics, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [Article DOI: http://dx.doi.org/10.1021/om401044z].en_US
dc.subjectDRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
dc.titleSynthesis, optical resolution, and stereochemical properties of a rationally designed chiral C–N palladacycleen_US
dc.typeJournal Article
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.description.versionAccepted versionen_US

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