| 昆虫性信息的结构鉴定与合成 XXVII: (5R, 6S)-(-)-及(5S, 6R)-(+)-淡色库蚊产卵引诱性信息素的立体选择性合成与手性亚砜不对称加成的立体化学 |
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| 引用本文： | 周维善,程杰飞,林国强.昆虫性信息的结构鉴定与合成 XXVII: (5R, 6S)-(-)-及(5S, 6R)-(+)-淡色库蚊产卵引诱性信息素的立体选择性合成与手性亚砜不对称加成的立体化学[J].化学学报,1988,46(3):274-280. |
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| 作者姓名： | 周维善 程杰飞 林国强 |
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| 作者单位： | 中国科学院上海有机化学研究所 |
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| 摘 要： | 从R-(-)-正十三烯-3-醇2所得的R-(+)-醛5, 与R-(+)亚砜化合物6的不对称醇醛缩合得7a和7b(30:1). 7a经一系列转化得1a, 从(5S, 6R)-14出发, 经两次构型翻转5S,6R)-15→(5S, 6S)-16和(5S, 6S)-17→(5R, 6S)-14], 得1a的对映体1b. 光学活性α-苄氧基醛5与手性亚砜的不对称醇醛缩合, 受手性亚砜的1,3-不对称诱导控制, 而不是受醛5的1,2-不对称诱导控制.
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| 关 键 词： | 亚砜 立体化学 立体选择性 昆虫激素 性信息素 手征性 库蚊属 淡色库蚊 不对称反应 |
Studies on the Identification and syntheses of insect pheromone XXVII: Stereoselective synthesis of (5R, 6S)-(-) and (5S, 6R)-(+)-mosquito oviposition attractant pheromone and stereochemistry of asymmetric addition of a chiral sulfoxide to a chiral aldehy |
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| ZHOU WEISHAN,CHENG JIEFEI,LIN GUOQIANG.Studies on the Identification and syntheses of insect pheromone XXVII: Stereoselective synthesis of (5R, 6S)-(-) and (5S, 6R)-(+)-mosquito oviposition attractant pheromone and stereochemistry of asymmetric addition of a chiral sulfoxide to a chiral aldehy[J].Acta Chimica Sinica,1988,46(3):274-280. |
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| Authors: | ZHOU WEISHAN CHENG JIEFEI LIN GUOQIANG |
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| Abstract: | The title pheromones I and II were prepared starting from (R)-(-)-tridec-1-en-3-ol via asym addition of a chiral sulfoxide 4-MeC6H4SOCH2CO2CMe3 to (R)-(+)-Me(CH2)9CH(OCH2Ph)CHO. |
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| Keywords: | SULFOXIDE STEREOCHEMISTRY STEREOSELECTIVITY INSECT HORMONE SEX PHEROMONE CHIRALITY CULEX MOSQUITO |
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