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

该职业奖支持西华盛顿大学化学系Gregory W. O'Neil教授的研究小组探索β -酰基氧基砜作为一种通用的烯烃保护基团策略的使用，重点是在烯烃复分解中使用它来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基氧基砜的复分解/消除序列作为一种多功能和立体选择性的方法，用于合成具有挑战性的多烯和碳环目标。其他预期的见解包括对钐介导的酰基氧基砜消除的详细机制理解，以及对一般预测烯烃复分解模型的进一步数据。使用所提出的策略可以很容易地制备目标的例子包括一类称为多不饱和长链烯酮（PULCAs）的藻类脂质。一系列的这些化合物将被合成和探索，以推进藻类生物柴油技术的发展。这项工作大部分由本科生进行，为这些学生提供现代合成有机技术的宝贵训练。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，提高学生对化学和相关STEM领域的参与。通过与当地可再生能源行业合作，建立一个涉及高中和大学学生的跨学科生物柴油合作实验，将部分实现这一目标。拟议研究的具体结果也将纳入PI开发的“生物燃料”课程和拟议的顶点课程“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。

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.