Semipinacol重排反应研究
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摘要
“多官能团化季碳中心”结构单元,广泛存在于各种具有生物活性的天然产物及其它重要的功能性有机分子中,其立体选择性合成是有机化学中的重要研究内容。Semipinacol重排反应由于在构建该结构单元方面的高度立体控制,正逐渐成为有机化学家广泛适用的方法。本小组在多功能串联Semipinacol重排反应的研究上取得了显著的成果,本论文延续了这一研究方向,完成了一些多官能团化季碳中心立体选择性的构建,并取得了一系列突破性的进展,其主要包括以下两个部分内容:
一、硅胶促进的烯丙醇环氮化/Semipinacol重排串联反应。该反应从简单易得的烯丙醇出发首次实现了非金属促进此类[1,2]-迁移重排过程,以非常高的非对映选择性、较好的收率一步构建含有季碳的Mannich碱。突破了前期工作中环氮化收率很低的瓶颈,同时为环氮醇Semipinacol重排串联反应研究开辟了新的内容。
二、有机催化对映选择性Semipinacol重排反应。该反应成功地把近十年来飞速发展的有机催化的概念和Semipinacol重排反应有效地结合起来,实现了有机催化不对称Semipinacol重排反应,以高达97%的ee值实现了多官能团化螺环季碳的手性构建。该研究为螺环季碳的构建提供了一条新的途径,也为Semipinacol重排反应拓展出一个新的具有重要合成应用价值的研究领域。
The multi-functional unit with quaternary carbon extensively exists in biologically significant natural products and other important organic molecules,and it is of major importance to stereoselectively construct this unit in organic chemistry.The semipinacol rearrangement is becoming a widely applied reaction in organic synthesis allowing the stereoselective construction of these units.Some significant progresses have been made by our group on this field.This thesis finished some breakthroughs in the high efficient and enantioselective construction of multi-functional unit with quaternary carbon and correspondingly a series of progressive results were achieved in this research field.The following two parts are mainly included:
1.Tandem aziridination/rearrangement reaction of allylic alcohols induced by silica gel.On the basis of this methodology,an efficient and highly stereoselective approach to various 2-quaternary Mannich bases have been put in place from simple allylic alcohols in high yield,overcoming the limit of low yield of aziridination on the previous method.This kind of[1,2]-rearrangement process was firstly realized by silica gel,and expanded the research field of the tandem semipinacol rearrangement of aziridino alcohols.
2.Enantioselective semipinacol rearrangement catalyzed by organocatalyst.The semipinacol rearrangement and fast developing concept of organocatalyst in last decade were combined successively,achieving asymmetric semipinacol rearrangement catalyzed by organocatalyst.Multi-functional spiro-quaternary centers were synthesized in up to 97%ee by this new method.A new and attractive research field with a good prospect of development and utilization was exploited on semipinacol rearrangement.
一、硅胶促进的烯丙醇环氮化/Semipinacol重排串联反应。该反应从简单易得的烯丙醇出发首次实现了非金属促进此类[1,2]-迁移重排过程,以非常高的非对映选择性、较好的收率一步构建含有季碳的Mannich碱。突破了前期工作中环氮化收率很低的瓶颈,同时为环氮醇Semipinacol重排串联反应研究开辟了新的内容。
二、有机催化对映选择性Semipinacol重排反应。该反应成功地把近十年来飞速发展的有机催化的概念和Semipinacol重排反应有效地结合起来,实现了有机催化不对称Semipinacol重排反应,以高达97%的ee值实现了多官能团化螺环季碳的手性构建。该研究为螺环季碳的构建提供了一条新的途径,也为Semipinacol重排反应拓展出一个新的具有重要合成应用价值的研究领域。
The multi-functional unit with quaternary carbon extensively exists in biologically significant natural products and other important organic molecules,and it is of major importance to stereoselectively construct this unit in organic chemistry.The semipinacol rearrangement is becoming a widely applied reaction in organic synthesis allowing the stereoselective construction of these units.Some significant progresses have been made by our group on this field.This thesis finished some breakthroughs in the high efficient and enantioselective construction of multi-functional unit with quaternary carbon and correspondingly a series of progressive results were achieved in this research field.The following two parts are mainly included:
1.Tandem aziridination/rearrangement reaction of allylic alcohols induced by silica gel.On the basis of this methodology,an efficient and highly stereoselective approach to various 2-quaternary Mannich bases have been put in place from simple allylic alcohols in high yield,overcoming the limit of low yield of aziridination on the previous method.This kind of[1,2]-rearrangement process was firstly realized by silica gel,and expanded the research field of the tandem semipinacol rearrangement of aziridino alcohols.
2.Enantioselective semipinacol rearrangement catalyzed by organocatalyst.The semipinacol rearrangement and fast developing concept of organocatalyst in last decade were combined successively,achieving asymmetric semipinacol rearrangement catalyzed by organocatalyst.Multi-functional spiro-quaternary centers were synthesized in up to 97%ee by this new method.A new and attractive research field with a good prospect of development and utilization was exploited on semipinacol rearrangement.
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