RUI: Catalyst Systems to Effect Asymmetric Induction in the Hydroamination of Olefins

RUI：在烯烃加氢胺化中实现不对称诱导的催化剂体系

• 批准号: 1566124
• 负责人: Anna Wenzel
• 金额: $ 19.31万
• 依托单位: Claremont McKenna College
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2016
• 资助国家: 美国
• 起止时间: 2016-09-01 至 2020-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1566124&HistoricalAwards=false
• 关键词: RUI; Catalyst; Systems; Effect; Asymmetric

The Chemical Catalysis Program of the Chemistry Division supports the research project by Professor Wenzel. Professor Wenzel is a faculty member at the W. M. Keck Science Department at Claremont McKenna College. She is developing new molecules to catalyze selective hydroamination of alkenes. Hydroamination reactions are an efficient route for the preparation of amines, a common structure found in pharmaceutical and agrichemical products. The reactions are focused on making the synthesis sustainable. The catalyst molecules are designed to be readily available and to support robust reactions. The study is uncovering a wealth of fundamental information regarding the factors governing reaction design. The research is conducted entirely by undergraduate students. Professor Wenzel's program is well-poised to address the ongoing deficiency of underrepresented groups in science. She has an excellent record in training underrepresented minority students and successfully encouraging them to pursue graduate studies in chemistry. This research outlines the preparation of chiral heterodonor phosphorous/thioether (P/S) and phosphorous/amine (P/N) ligands as alternatives to classically-used bisphosphines for coordination onto palladium, ruthenium, and copper. The chiral, bidentate ligands are equipped with strong and weak donor-heteroatom pairs (e.g., P/S or P/N) to utilize favorable electronics to strongly influence the stability and reactivity associated with stereochemistry-defining reaction intermediates. The new catalysts are evaluated in two types of hydroamination reactions: an intermolecular, asymmetric anti-Markovnikov hydroamination of unactivated olefins and the enantioselective, Markovnikov hydroamination of dienes to produce dihydroquinolines. It is through a robust program in the training of undergraduate researchers that Professor Wenzel tries to advance of science as well as the education of future science professionals.

化学系的化学催化计划支持Wenzel教授的研究项目。Wenzel教授是W. M.克莱蒙麦肯纳学院凯克科学系。她正在开发新的分子来催化烯烃的选择性加氢胺化。加氢胺化反应是制备胺的有效途径，胺是药物和农药产品中常见的结构。反应的重点是使合成可持续。 催化剂分子被设计为易于获得并支持稳健的反应。这项研究揭示了大量关于控制反应设计的因素的基本信息。这项研究完全由本科生进行。温泽尔教授的计划是做好准备，以解决在科学代表性不足的群体的持续不足。 她在培训代表性不足的少数民族学生方面有着出色的记录，并成功地鼓励他们攻读化学研究生课程。 本研究概述了制备手性杂供体磷/硫醚（P/S）和磷/胺（P/N）配体作为经典使用的双膦配位到钯，钌和铜的替代品。手性双齿配体配备有强和弱供体-杂原子对（例如，P/S或P/N）以利用有利的电子来强烈影响与立体化学限定的反应中间体相关的稳定性和反应性。在两种类型的加氢胺化反应的新催化剂进行了评估：分子间的，不对称的反马尔可夫氢胺化未活化的烯烃和对映选择性，马尔可夫氢胺化的二烯，以产生二氢喹啉。这是通过一个强大的计划，在本科研究人员的培训，温泽尔教授试图推进科学以及未来的科学专业人士的教育。