New Catalytic Asymmetric Methods to Control Axial Chirality in Allenes

控制艾伦轴向手性的新催化不对称方法

基本信息

  • 批准号:
    1362953
  • 负责人:
  • 金额:
    $ 39万
  • 依托单位:
  • 依托单位国家:
    美国
  • 项目类别:
    Continuing Grant
  • 财政年份:
    2014
  • 资助国家:
    美国
  • 起止时间:
    2014-09-01 至 2018-08-31
  • 项目状态:
    已结题

项目摘要

With this Award from the Chemical Catalysis Program in the Division of Chemistry, Professor Frantz at the University of Texas at San Antonio is developing new chemical reactions to meet unmet synthetic needs that broadly impact the efficient manufacture of small molecules in areas such as pharmaceuticals, agricultural products, and advanced materials. As a part of this proposed research program, Professor Frantz has developed excellent opportunities to train students at all levels in the development of modern methodologies in asymmetric catalysis and organic synthesis. The techniques and knowledge gained during the development of this research will improve students' competitive edge in both industrial and academic careers. In addition, recruitment and participation by underrepresented minorities and groups, Hispanics and women, is a key component of the supported project.This project focuses on the discovery and development of new catalytic methods to synthesize chiral allenes from sustainable raw materials. In the proposed funding period, various metal-based catalysts in combination with chiral phosphorous-based ligands are being evaluated for their ability to promote an enantioselective beta-hydride elimination from intermediate cationic vinyl Pd(II)-complexes to efficiently control the axial chirality in allenes. Specific explorations focus on several transformations to explore this new chemistry including tandem transmetalation/beta-hydride elimination of vinyl boranes and intramolecular tandem carbometallations/beta-hydride eliminations of alkynes. A key feature of these transformations is the exploitation of a reaction manifold that is typically viewed as an unproductive side-reaction (beta-hydride eliminations) in most metal-catalyzed processes to a new productive avenue in asymmetric catalysis and synthesis.
凭借化学部化学催化计划的这一奖项,德克萨斯大学圣安东尼奥分校的Frantz教授正在开发新的化学反应,以满足未满足的合成需求,这些需求广泛影响了制药,农产品和先进材料等领域小分子的有效制造。 作为该研究计划的一部分,Frantz教授为培养各级学生提供了极好的机会,以发展不对称催化和有机合成的现代方法。 在本研究的发展过程中获得的技术和知识将提高学生在工业和学术生涯中的竞争优势。 此外,招募和参与代表性不足的少数民族和群体,西班牙裔和妇女,是支持项目的一个关键组成部分。该项目的重点是发现和开发新的催化方法,从可持续的原料合成手性丙二烯。 在拟议的资助期内,正在评估各种金属基催化剂与手性磷基配体的组合,以促进中间体阳离子乙烯基Pd(II)-络合物的对映选择性β-氢化物消除,从而有效控制联烯中的轴向手性。 具体的探索集中在几个转换,探索这种新的化学,包括串联transmetalation/β-氢化物消除乙烯基硼烷和分子内串联carbenylation/β-氢化物消除炔。这些转化的一个关键特征是利用在大多数金属催化过程中通常被视为非生产性副反应(β-氢化物消除)的反应歧管,以在不对称催化和合成中开辟新的生产途径。

项目成果

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