Selective Hydroxylation Of Alkenes And The Synthesis Of α-Carboxy-cis Olefin

α, β-unsaturated alcohol contains two function groups with high chemical activity,i. e. double bond and hydroxyl group.They provide the competition during the reactions like addition, esterification, etherification, etc., and halogenated reaction which is an important intermediate in synthetic perfumes, pesticides, surfactants and pharmaceuticals, etc. Many different ways have been researched to synthesize the unsaturated alcohol,but it is a research focus in the field of organic synthetic chemistry research using the olefin as the starting material to synthesize α,β-unsaturated alcohol.The paper will focus on two aspects:1.Two different paths to synthesize the α,β-unsaturated alcohol have been explored using the olefin as the starting material.2.In order to obtain the D, E blocks of the Yohimbine, polyfunctional phosphorus Ylide reagent has been prepared out which will be used to synthesize the Z-type olefin by the Wittig Reaction.This article describes two paths to prepare α,β-unsaturated alcohols.Route 1 prepare ester as a reaction intermediate, which will be hydrolysis to give the corresponding unsaturated alcohol.Cyclohexene is used as a substrate in the experiments. The product yields are detected by HPLC in the oxidation reaction which use different peroxide as the oxidant.The results show that the yield of cyclohex-2-en-1-yl benzoate is 49% which is the highest when tert-butyl benzoperoxoate is used as the oxidant.There is no product detected when benzoic acid and CYHPO are used as the oxidant.In Route 2 peroxide will be reduced after olefins have been converted to organic hydroperoxide.R-TPP type porphyrin is used as a catalyst to obtain the organic hydroperoxide, which will be decomposed reduction by the Zeolite Catalysts Cu-OMS-1 to α, β-unsaturated alcohol.2,3-dimethylbut-2-ene is a representative in the experiment exploration process.The reduction decomposition reaction of the hydrogen peroxide isolated is explored later.A standard curve line of 2,3-dimethylbut-3-en-2-ol which has been purified will be applied to the quantitative reaction. The corresponding α, β-unsaturated alcohol will be prepared when cyclohexene,2-methyl-2-butene, citronellol and other substrates participate in the reaction.There are many different paths to prepare the Yohimbine. Our team has designed a new route in which the D,E blocks are important intermediate.Given multi-functional structure of Z-type olifin which contain three double bonds is the key of the route. By using methyl crotonate and diphenyl chlorophosphate as the starting material, a novel poly functional phosphorus Ylide reagent has been prepared and isolated which can be used for the selective synthesis of Z-type olefin in the experiment. Our work provide a prerequisite for the synthesis of the D,E blocks.