CAREER: New Synthetic Applications of Trichloromethyl Carbinols

该项目将继续开发使用宝石-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。已建立的获得此类材料的路线通常需要低效的反应步骤、昂贵的试剂或危险的反应条件。将探索建立更安全和更短的方法来同系化羧酸和从现成的三氯甲基甲醇中制备β-氨基酸、脱氧-C-糖苷和氨基-C-糖苷的方法。将从产率、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等方面对合成产物进行评价。结构-反应性分析和在仔细调整的反应条件下的产物分析还将展示具体参数如何影响每种方法中涉及的瞬时GEM-二氯环氧化物中间体的形成和反应性。通过这一奖项，有机和高分子化学项目正在支持阿拉巴马大学化学系教授蒂莫西·斯诺登的研究。斯诺登教授的研究工作围绕着提供更安全、更有效的方法来制备合成的多功能取代羰基化合物，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、操作安全和材料成本方面提供显著改善。该方法的成功开发将对学术研究项目以及制药、农用化学品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.