CAREER: New Synthetic Applications of Trichloromethyl Carbinols

该项目将继续开发涉及偕二氯环氧化物中间体的方法，以安全和经济地制备取代的羰基化合物和生物分子类似物。获得这些材料的既定途径通常需要低效的反应步骤、昂贵的试剂或危险的反应条件。将探讨研究如何建立更安全和更短的方法，从容易获得的三氯甲基甲醇中同系化羧酸和制备β-氨基酸、脱氧-C-糖苷和氨基-C-糖苷。所得产物将根据产率、制备成本以及设计的反应步骤的立体选择性和区域选择性进行评估。在仔细调整的反应条件下进行的结构-反应性分析和产品分析也将证明特定参数如何影响每种方法中涉及的瞬态偕二氯环氧化物中间体的形成和反应性。 有了这个奖项，有机和高分子化学计划正在支持化学系教授蒂莫西·斯诺登在亚拉巴马大学的研究。 斯诺登教授的研究工作围绕提供更安全，更有效的方法来制备合成通用的取代羰基化合物，以及具有治疗价值的非天然氨基酸和杂环。 与目前采用的方法相比，这些方法将在环境影响、操作安全性和材料成本方面提供显著的改善。 该方法的成功开发将对学术研究计划以及制药，农业化学和材料科学领域的合成产生影响。

This project will continue the development of methods involving gem-dichloroepoxide intermediates for the safe and economical preparation of substituted carbonyl compounds and biomolecule analogs. Established routes to such materials generally require inefficient reaction steps, expensive reagents, or dangerous reaction conditions. Studies to establish safer and shorter methods for homologating carboxylic acids and preparing beta-amino acids, deoxy-C-glycosides and amino-C-glycosides from readily available trichloromethyl carbinols will be explored. The resultant products will be evaluated in terms of yield, preparation cost, and the stereo- and regioselectivities of devised reaction steps. Structure-reactivity analyses and product analyses under carefully adjusted reaction conditions will also demonstrate how specific parameters affect the formation and reactivity of the transient gem-dichloroepoxide intermediates involved in each method. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Timothy Snowden of the Department of Chemistry at The University of Alabama. Professor Snowden's research efforts revolve around providing safer and more efficient methods to prepare synthetically versatile substituted carbonyl compounds, and therapeutically valuable unnatural amino acids and heterocycles. These methods will offer marked improvements in environmental influence, operational safety, and materials costs over currently employed approaches. Successful development of the methodology will have an impact on synthesis in academic research programs and in the pharmaceutical, agrochemical, and materials science fields.