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頁籤選單縮合
題 名 | Preparation of Chiral Phosphorus(V) Reagents and Their Uses with Borane in the Enantioselective Reduction of Ketones |
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作 者 | 陳國祥; 徐睿良; 楊文彬; 方俊民; 李錦祥; 劉怡弘; 王瑜; | 書刊名 | Journal of the Chinese Chemical Society |
卷 期 | 46:5 1999.10[民88.10] |
頁 次 | 頁797-810 |
分類號 | 346.113 |
關鍵詞 | 酮; 硼烷; 磷試劑; 麻黃鹼; Phosphorus(V) reagents; Borane; Ketones; Ephedrine; Enantioselective; Reduction; |
語 文 | 英文(English) |
英文摘要 | Chiral pentavalent phosphorus reagents 5-17 were prepared from POCl�� and ephedrine (or the related α -amino alcohols), followed by substitution with nucleophiles of phenylmagnesium bromide, alcohols, amines, diamines and triamines. The substitution reactions occurred in a stereospecific manner with retention of the configuration at the phosphorus center. The structures of these phosphorus(V) reagents were determined by spectral methods and verified by X-ray diffraction in several instances. These phosphorus(V) reagents were used with borane/dimethylsulfide complex in the enantioselective reduction of aromatic, aliphatic and heterocyclic ketones. The phosphorus(V) reagents likely functioned as Lewis bases to react with borane, forming in situ zwitterionic species as the chiral reducing agents. The reactions were generally carried out at 0 ℃ in tetrahydrofuran solution with a molar ration of ketone/borane/phosphoramidate = 1:1:0.2 to afford secondary alcohols with modest enantioselectivity, up to 67% ee in the reduction of 4'-methylacetophenone. |
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