Application of Sulfinamides in Synthesis and Catalysis

亚磺酰胺类化合物在合成与催化中的应用

• 批准号: 1049571
• 负责人: Jonathan Ellman
• 金额: $ 48万
• 依托单位: Yale University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2011
• 资助国家: 美国
• 起止时间: 2011-02-01 至 2014-01-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1049571&HistoricalAwards=false
• 关键词: Application; Sulfinamides; Synthesis; Catalysis

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Jonathan Ellman of the Department of Chemistry at Yale University will develop methods for the asymmetric synthesis of amine-containing compounds using tert-butanesulfinamide. Powerful new methods for the efficient asymmetric synthesis of alpha-branched amines will be developed through the highly functional group compatible addition of organozinc and organoboron reagents to N-tert-butanesulfinyl imines. New sulfinamide-based organocatalysts will also be developed as a general new class of catalysts for the highly efficient synthesis of amine-containing compounds applicable to the production of bioactive drugs and agrochemicals.The proposed work has broad impact because more than 80% of all drugs and drug candidates contain amine functionality, and many of these amine-containing compounds are also chiral. tert-Butanesulfinamide chemistry, developed in Professor Ellman's lab largely with NSF support, is one of the most extensively used methods for the preparation of amine containing compounds in the pharmaceutical, biotechnology and agrochemical industries as well as in academic chemical biology research. The research proposed here could further enhance the utility of this chemistry and consequently accelerate scientific advances, including the discovery of new drugs to treat unmet medical conditions. Moreover, the proposed work will involve training undergraduate and graduate students, including those from groups currently underrepresented in the sciences.

在这个由化学部化学合成计划资助的项目中，耶鲁大学化学系的Jonathan Ellman教授将开发使用叔丁亚磺酰胺不对称合成含胺化合物的方法。 通过有机锌和有机硼试剂与N-叔丁基亚磺酰亚胺的高官能团相容加成反应，将开发出高效不对称合成α-支链胺的新方法。新的亚磺酰胺基有机催化剂也将被开发作为一种通用的新型催化剂，用于高效合成适用于生产生物活性药物和农用化学品的含胺化合物。拟议的工作具有广泛的影响，因为超过80%的所有药物和候选药物含有胺官能团，并且这些含胺化合物中的许多也是手性的。叔丁亚磺酰胺化学是在埃尔曼教授的实验室中主要在美国国家科学基金会的支持下开发的，是制药、生物技术和农用化学工业以及学术化学生物学研究中制备含胺化合物最广泛使用的方法之一。本文提出的研究可以进一步提高这种化学的实用性，从而加速科学进步，包括发现治疗未满足的医疗条件的新药。 此外，拟议的工作将涉及培训本科生和研究生，包括那些目前在科学领域代表性不足的群体。