Development of the practical organic reactions based on the π-coordination of alkyne to Lewis acid

基于炔烃与路易斯酸π配位的实用有机反应的发展

基本信息

  • 批准号:
    12554028
  • 负责人:
  • 金额:
    $ 8.83万
  • 依托单位:
  • 依托单位国家:
    日本
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
  • 财政年份:
    2000
  • 资助国家:
    日本
  • 起止时间:
    2000 至 2001
  • 项目状态:
    已结题

项目摘要

Lewis acid mediated chelatipn control is one of the most fundamental and efficient methodologies for effecting the selective carbon-carbon bond formation in modern organic synthesis. It is well accepted that the chelation-controlled feactions proceed through the coordination of a lone pair of heteroatoms, such as an oxygen of an aldehyde br a nitrogen atom of an imine, to a Lewis acid, which is recognized as a σ-σtype chelation. On the contrary, we found that chemo- and regioselective reactions of certain alkynyl and alkenyl aldehydes were accomplished through a σ-π chelation between a lone pair of the carbonyl compounds and π-electrons of the C-C multiple bond. We also found that the chemoselective ring opening of alkynyl epoxides in the co-existence of the corresponding alkyl epoxides is achieved in a Me_3Al mediated reaction with alkynyl lithium reagents; this interesting chemoselectivity is most probably a reflection of bidentate complexation to an n-electron pair of the oxygen atom of the epoxide and π-electrons of the C-C triple bond.
Lewis酸介导的络合控制是现代有机合成中影响选择性碳-碳键形成的最基本和最有效的方法之一。人们普遍认为,络合控制的作用是通过一对孤对杂原子的配位来进行的,例如醛的氧原子和亚胺的氮原子与路易斯酸的配位,这被认为是σ-σ类型的络合。相反,我们发现某些炔基和烯基醛的化学和区域选择性反应是通过一对孤立的羰基化合物与C-C多键的σ-π-电子之间的π络合完成的。我们还发现,在相应的烷基环氧化物的共存下,炔基环氧化物的化学选择性开环是在Me_3Al介导的与炔基锂试剂的反应中实现的;这种有趣的化学选择性很可能是对环氧化物的氧原子和C-C三键的π-电子的n电子对的双齿络合的反映。

项目成果

期刊论文数量(64)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Asao, N., Ohishi, T., Sato, K., Yamamoto, Y.: "σ-π Chelation-Controlled Stereoselective Hydrosilylation of Ketones"Journal of the American Chemical Society. 123. 6931-6932 (2001)
Asao, N.、Ohishi, T.、Sato, K.、Yamamoto, Y.:“σ-π 螯合控制的酮的立体选择性氢化硅烷化”美国化学会杂志 123. 6931-6932 (2001)。
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E. Yoshikawa, M. Kasahara, N. Asao, Y. Yamamoto: "Lews acid-Catalyzed trans-Carbosilylation of Alkynes with Propargyl and Allenyltrimethylsilanes"Tetrahedron Lett.. 41. 4499-4502 (2000)
E. Yoshikawa、M. Kasahara、N. Asao、Y. Yamamoto:“路易斯酸催化的炔烃与丙炔基和烯基三甲基硅烷的反式碳甲硅烷基化”Tetrahedron Lett.. 41. 4499-4502 (2000)
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N. Asao, T. Shimada, Y. Yamamoto: "Lewis Acid Catalyzed Stereoselective Carbosilylation. Intramolecular trans-Vinylsilylation and trans-Arylsilylation of Unactivated Alkynes"J. Am. Chem. Soc.. 123. 10899-10902 (2001)
N. Asao,T. Shimada,Y. Yamamoto:“路易斯酸催化的立体选择性碳硅烷化。未活化炔烃的分子内反式乙烯基硅烷化和反式芳基硅烷化”J。
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    0
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N. Asao, T. Asano, Y. Yamamoto: "Do more electrophilic aldehydes/ketones exhibit higher reactivity toward nucleophiles in the presence of Lewis acids?"Angew. Chem., Int. Ed.. 40. 3206-3208 (2001)
N. Asao、T. Asano、Y. Yamamoto:“在路易斯酸存在下,更多的亲电醛/酮对亲核试剂表现出更高的反应性吗?”Angew。
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Asao, N., Kasahara, T., Yamamoto, Y.: "σ-πChelation-controlled chemoselective ring openings of epoxides"Tetrahedron Letters. 42. 7903-7905 (2001)
Asao, N.、Kasahara, T.、Yamamoto, Y.:“环氧化物的 σ-π 螯合控制的化学选择性开环”Tetrahedron Letters 42. 7903-7905 (2001)。
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YAMAMOTO Yoshinori其他文献

YAMAMOTO Yoshinori的其他文献

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{{ truncateString('YAMAMOTO Yoshinori', 18)}}的其他基金

Deuterium isotope effect for high performance organic solar cells
高性能有机太阳能电池的氘同位素效应
  • 批准号:
    25620021
  • 财政年份:
    2013
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Challenging Exploratory Research
Fabrication of nanoporous metal catalysts by a dealloying method for molecular transformations
通过分子转化脱合金方法制备纳米多孔金属催化剂
  • 批准号:
    23245020
  • 财政年份:
    2011
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (A)
Evaluation of the starch accumulating palms in the Tropics as the resource of ethanol production
热带地区积累淀粉的棕榈树作为乙醇生产资源的评价
  • 批准号:
    23405018
  • 财政年份:
    2011
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Development of Gold-and Palladium-catalyzed New Transformations via Modification of Ligands
通过配体修饰开发金和钯催化的新转化
  • 批准号:
    20350015
  • 财政年份:
    2008
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
STRCH ACCUMULATING PALMS IN THE TROPICS, ESTIMATION OF ITS PRODUCTIVITY AND CLARIFICATION OF STARCH PROPERTIES
STRCH 在热带地区积累棕榈树,估算其生产力并澄清淀粉特性
  • 批准号:
    18405019
  • 财政年份:
    2006
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Development of Sustainable Process for Molecular Transformation Using Lewis Acid/Transition Metal Catalysts
使用路易斯酸/过渡金属催化剂开发可持续的分子转化工艺
  • 批准号:
    14002001
  • 财政年份:
    2002
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Specially Promoted Research
Studies on Premature Heading and Its Prevent Methods for Early Season Culture and Planting of Extremely Early Rice Cultivars in Warm South-west Japan
温暖的西南部地区极早稻品种早抽穗及其防治方法的研究
  • 批准号:
    14560012
  • 财政年份:
    2002
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Basic Study on Super Panicle Weight Type Varieties in Rice
水稻超粒重型品种的基础研究
  • 批准号:
    11695079
  • 财政年份:
    1999
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Studies on the Characteristics of Differentiation and Degeneration of Spikelets and Grain-filling in High-yielding Rice Cultivars with Large Panicles
大穗水稻高产品种小穗分化退化及灌浆特性研究
  • 批准号:
    11660018
  • 财政年份:
    1999
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Development of the novel C-C bond forming reactions using homogeneous transition metal catalysts
使用均相过渡金属催化剂开发新型 C-C 键形成反应
  • 批准号:
    09304069
  • 财政年份:
    1997
  • 资助金额:
    $ 8.83万
  • 项目类别:
    Grant-in-Aid for Scientific Research (A)

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