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Asymmetric synthesis of a chiral arsinophosphine via a metal template promoted asymmetric Diels-Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine |
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| Authors: | Kien-Wee Tan Yongxin Li Pak-Hing Leung |
| Institution: | a Division of Chemistry and Biological Chemistry, Nanyang Technological University, Nanyang Walk, Singapore 637616, Singapore b Department of Chemistry, National University of Singapore, Kent Ridge, Singapore 119260, Singapore |
| Abstract: | The asymmetric Diels-Alder reaction between 2-furyldiphenylarsine and diphenylvinylphosphine was achieved stereospecifically by utilizing an organoplatinum reaction promoter containing the ortho-metalated (R)-(1-(dimethylamino) ethyl)-naphthalene as the chiral auxiliary. The optically pure (+)-As-P heterobidentate cycloadduct could be liberated from the template product by successive treatment with concentrated hydrochloric acid and aqueous potassium cyanide. |
| Keywords: | Asymmetric Diels-Alder Chiral metal template Optically active arsinophosphine Vinylphosphine Arsine substituted furan |
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