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 DMPP S 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 ligand as the major product. Throughout the cycloaddition reaction, DMPP functions chemoselectively as the cyclic diene whilst DMPP S assumes the role of dienophile. The absolute stereochemistry of the novel chiral heteroditopic 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 |
本文献已被 ScienceDirect 等数据库收录! |