CAREER: Beta-Acyloxysulfones as an Enabling Alkene Protecting Group in Synthesis

职业生涯：β-酰氧基砜作为合成中的烯烃保护基

• 批准号: 1151492
• 负责人: Gregory O'Neil
• 金额: $ 43万
• 依托单位: Western Washington University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2012
• 资助国家: 美国
• 起止时间: 2012-08-15 至 2018-12-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1151492&HistoricalAwards=false
• 关键词: CAREER; Beta; Acyloxysulfones; Enabling; Alkene

This CAREER award supports the research group of Professor Gregory W. O'Neil of the Department of Chemistry at Western Washington University to explore the use of beta-acyloxysulfones as a general alkene protecting-group strategy, with an emphasis on its use in olefin metathesis to prepare important polyene compounds unobtainable by standard metathesis technology. Early work will investigate an acyloxysulfone metathesis/elimination sequence as a versatile and stereoselective approach for the construction of synthetically challenging polyene and carbocyclic targets. Additional expected insights include a detailed mechanistic understanding of samarium-mediated acyloxysulfone elimination and further data toward a general predictive olefin metathesis model. Examples of targets that can be readily prepared using the proposed strategy include a class of algal lipids known as polyunsaturated long-chain alkenones (PULCAs). A series of these compounds are to be synthesized and explored for the advancement of algal biodiesel technology. Much of this work is to be conducted by undergraduate students, providing these students with valuable training in modern synthetic organic techniques. This research is closely integrated with an educational plan aimed at leveraging broad student interest in renewable energy to increase student participation in chemistry and related STEM fields. This is to be accomplished in part through the creation of a cross-discipline cooperative biodiesel experiment involving students at both the high school and college level in collaboration with local renewable energy industries. Specific results from the proposed research will also be incorporated into a "Biofuels" course developed by the PI and a proposed capstone "Chemistry of Energy" course. These courses are to be part of a new cross-college Clean Energy curriculum at Western Washington University.

这个职业奖支持格雷戈里W教授的研究小组。O 'Neil的研究，探索使用β-酰氧基砜作为一般的烯烃保护基策略，重点是其在烯烃复分解中的用途，以制备标准复分解技术无法获得的重要多烯化合物。 早期的工作将研究酰氧基砜复分解/消除序列作为一种通用的和立体选择性的方法，用于建设具有挑战性的多烯和碳环目标。其他预期的见解包括详细的机制理解钐介导的酰氧基砜消除和进一步的数据，对一般的预测烯烃复分解模型。 可以使用所提出的策略容易地制备的靶标的实例包括一类被称为多不饱和长链烯酮（PULCA）的藻类脂质。一系列此类化合物的合成和开发将为藻类生物柴油技术的发展做出贡献。这项工作的大部分将由本科生进行，为这些学生提供现代合成有机技术的宝贵培训。 这项研究与一项教育计划紧密结合，旨在利用学生对可再生能源的广泛兴趣，增加学生对化学和相关STEM领域的参与。这将部分通过创建一个跨学科的生物柴油合作实验来实现，该实验涉及高中和大学学生，并与当地可再生能源行业合作。 拟议研究的具体结果也将纳入PI开发的“生物燃料”课程和拟议的顶点“能源化学”课程。这些课程将成为西华盛顿大学新的跨学院清洁能源课程的一部分。