光学纯膦酸薄荷醇衍生物的制备及在立体选择性合成手性含磷化合物中的应用分析-有机化学专业论文.docxVIP

聊城大学硕士学位论文 聊城大学硕士学位论文 聊城大学硕士学位论文 聊城大学硕士学位论文 ii ii ABSTRACT Asymmetric P-C bonds are significant for organic synthesis, asymmetric catalysis and pharmacochemistry. Firstly this article deals with the significance and history of P-C bonds and chiral phosphorus compounds, followed with the introduction of modified method for synthesis of O-menthyl (Rp)-phenylphosphinate. Our research gave a high efficient method to get an important chiral phosphorus compound O-menthyl (Rp)-phenylphosphinate. The synthetic selectivity and yield for the formation of O-menthyl (Rp)-phenylphosphinate was studied, and a method for transformation of Sp isomer to Rp isomer was found, which improve efficiency and reduce cost of synthesis of O-menthyl (Rp)-phenylphosphinate. As starting material, the chiral phosphinate was used to synthesize a series of Rp and Sp O-menthyl arkylphenylphosphonates, respectively. P-H bond of chiral phosphinite can be converted to configration-retention P-S compounds in good yields and over 99% de value. Alkyl-substituted （Rp）-phosphonate can be achieved by reaction of P-S-R bonds compounds with organometallic reagents.In most cases, the stereoselectivity was high to over 99% de. In addition, (Rp)-phenylphosphinate can be stereoselectively converted to corresponding phenylphosphonochloridate, which reacts to organometallic reagents to get alkyl-substituted (Sp)-phosphonate with high selectivity. Alkyls can be introduced into phosphonate which include various carbon groups. In the article we improved the synthesis of phosphinate and completed the synthesis of Rp and Sp O-menthyl arkylphenylphosphonate, which is of significance for research on chiral compounds. Our work may be bear great value in the field of theorical and applicative chemistry. Keywords: chiral; phosphinate; P-C bonds; phosphonochloridate; phosphonate; P-S-C bonds 目 录 HYPERLINK \l _bookmark0 前 言 1 HYPERLINK \l _bookmark1 第一章 绪论 3 HYPERLINK \l _bookmark2 1.1 P-C 键有机磷化合物合成的意义和背景 3 HYPERLINK \l