Asymmetric Synthesis Using tert-Butanesulfinamide

本研究的重点是利用叔丁基亚磺酰胺化学方法高效、立体选择性地合成复合胺。 该项目的目标将包括利用金属催化的硼物种与胺的加成;探索与α，β-不饱和N-亚磺酰亚胺的加成;开发N-亚磺酰金属烯胺与迈克尔受体的反应以及随后对迈克尔加成产物的转化;表征和研究N-亚磺酰醛亚胺自缩合的应用;使用N-亚磺酰基脒合成高度官能化的胺，包括天然产物的不对称合成;发展对用于制备宽范围的亚磺酸酯的亚磺酰卤化物的动态动力学拆分的增强理解，有了这个更新奖，有机和高分子化学计划是支持乔纳森博士的研究和教育活动。他是加州大学伯克利分校化学系的Ellman博士。 Ellman教授将专注于开发使用叔丁亚磺酰胺化学制备高度官能化的手性胺的方法。 新方法将被整合到相关天然产物的不对称合成中。 由于超过75%的药物和候选药物含有胺官能团，该项目对制药和生物技术行业具有重要的广泛影响。 此外，该项目将为本科生和研究生提供出色的培训。

The focus of this research involves the use of tert-butanesulfinamide chemistry for the efficient, stereoselective synthesis of complex amines. The goals of the project will include using metal-catalyzed additions of boron species to amines; exploring additions to alpha, beta-unsaturated N-sulfinyl imines; developing reactions of N-sulfinyl metalloenamines with Michael acceptors with subsequent transformations upon the Michael addition products; characterizing and studying applications of N-sulfinyl aldemine self-condensation; using N-sulfinyl amidines in the synthesis of densely functionalized amines, including the asymmetric synthesis of natural products and; developing an enhanced understanding of the dynamic kinetic resolution of sulfinyl halides for the preparation of a broad range of sulfinate esters, sulfoxides and sulfinamides.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research and educational activities of Dr. Jonathan A. Ellman in the Department of Chemistry at the University of California, Berkeley. Professor Ellman will focus his work on developing methods for preparation of highly functionalized chiral amines using tert-butanesulfinamide chemistry. The new methodology will be integrated into the asymmetric synthesis of relevant natural products. Since over 75% of all drugs and drug candidates contain amine functionality, this project has important broader impacts for the pharmaceutical and biotechnology industries. Also, the project will offer excellent training to both undergraduate and graduate students.