Allene Directed Asymmetric Synthesis

丙二烯定向不对称合成

• 批准号: 9901319
• 负责人: James Marshall
• 金额: $ 47.5万
• 依托单位: University of Virginia Main Campus
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1999
• 资助国家: 美国
• 起止时间: 1999-06-01 至 2003-05-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9901319&HistoricalAwards=false
• 关键词: Allene; Directed; Asymmetric; Synthesis

The focus of this research is the examination of the synthetic utility of chiral allenylmetallic reagents of tin, boron, titanium, chromium and palladium. Particular attention will be focused on SE' additions to aldehydes as a route to enantioenriched propargylic and allenic carbinols. Among the issues to be addressed are: The conformational and regiochemical stability of chiral allenyl and propargyl organometallics, the stereochemistry and regiochemistry of SE' additions involving these reagents, the effect of ligands on the enantioselectivity and regioselectivity of SE' additions with these reagents and the possible applications of these reagents in natural products synthesis.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. James A. Marshall of the Department of Chemistry at the University of Virginia. Professor Marshall will focus his work on the development of new synthetic methodology for the preparation of chiral carbon compounds by the use of chiral allenyl reagents of tin, boron, titanium, chromium and palladium. These novel intermediates have potential for use in the construction of natural products of interest to the pharmaceutical and agricultural industries.

本研究的重点是考察手性联烯基金属试剂锡、硼、钛、铬和钯的合成应用。特别关注的是SE添加到醛中作为获得对映体富集的炔丙醇和联烯甲醇的途径。 需要解决的问题包括：手性联烯基和炔丙基有机金属化合物的构象和区域化学稳定性，涉及这些试剂的SE'加成反应的立体化学和区域化学，配体对SE'与这些试剂加成反应的对映选择性和区域选择性的影响以及这些试剂在天然产物合成中的可能应用。有机和高分子化学计划正在支持詹姆斯A。弗吉尼亚大学化学系的马歇尔说。 马歇尔教授的工作重点是开发新的合成方法，利用锡、硼、钛、铬和钯的手性联烯基试剂制备手性碳化合物。 这些新的中间体具有用于构建制药和农业工业感兴趣的天然产物的潜力。