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Asymmetric synthesis of a P-chiral heteroditopic ligand via chiral metal template promoted cycloaddition between 3,4-dimethyl-1-phenylphosphole and its sulfonated analog
Authors:Sumod A Pullarkat  Mengtao Ma  Lip Lin Koh  Pak-Hing Leung
Institution:a Division of Chemistry and Biological Chemistry, Nanyang Technological University, Nanyang Walk 637616, Singapore
b Department of Chemistry, National University of Singapore, Kent Ridge 119260, Singapore
Abstract:The asymmetric 4+2] Diels-Alder reaction involving 3,4-dimethyl-1-phenylphosphole, DMPP, as the cyclic diene and its P-sulfonated analogue DMPPdouble bond; length as m-dashS as the dienophile was carried out by utilizing the palladium(II) template complex containing ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary. The reaction proceeded regiospecifically and stereoselectively to give corresponding phosphanorbornene Image ligand as the major product. Throughout the cycloaddition reaction, DMPP functions chemoselectively as the cyclic diene whilst DMPPdouble bond; length as m-dashS assumes the role of dienophile. The absolute stereochemistry of the novel chiral heteroditopic Image ligand was established by means of single crystal X-ray diffraction analysis.
Keywords:Asymmetric cycloaddition  Chiral metal template  Heteroditopic ligand  Chiral " alt="Image" title="Image" src="http://ars  els-cdn  com/content/image/1-s2  0-S0022328X06002439-fx3   ligand" target="_blank">gif"> ligand
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