2-吲哚甲醇平台分子参与的催化不对称反应研究进展  

Advances in Catalytic Asymmetric Reactions Using 2-Indolylmethanols as Platform Molecules

作　　者：张洪浩 石枫 Zhang Honghao;Shi Feng(School of Petrochemical Engineering,Changzhou University,Changzhou,Jiangsu 213164;School of Chemistry and Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116)

机构地区：[1]常州大学石油化工学院,江苏常州213164 [2]江苏师范大学化学与材料科学学院,江苏徐州221116

出　　处：《有机化学》2022年第10期3351-3372,共22页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.22125104,21831007,22001120);江苏省自然科学基金(No.BK20200297)资助项目。

摘　　要：吲哚骨架构成了众多天然产物、药物、农药、功能材料的核心结构单元,所以,手性吲哚类化合物的高效、高对映选择性合成已经成为有机化学领域的重要研究内容之一.由于传统的吲哚反应性单一,其参与的催化不对称反应类型有限,导致所构建的手性吲哚骨架的类型单一.为了解决这些挑战性问题,化学工作者通过在吲哚环上引入简单的官能团,得到一系列官能团化的吲哚衍生物,即吲哚类平台分子,作为构建手性吲哚骨架的高效合成砌块.其中,2-吲哚甲醇是一类重要的平台分子,其设计思路是通过在吲哚环的C2位引入羟甲基来改变吲哚环的反应性和反应位点.该类平台分子既可以作为亲电试剂,又可以作为亲核试剂,还可以作为多碳合成砌块参与催化不对称反应.所以,2-吲哚甲醇平台分子的设计与开发,为手性吲哚类化合物的高效、高对映选择性合成提供了新策略.归纳并评述了该类平台分子参与的催化不对称反应的研究进展,将为新型吲哚类平台分子的设计与应用提供新的思路.Indole-based chiral heterocycles constitute a class of important heterocyclic compounds that are found in numerous natural products, pharmaceuticals, pesticide, and functional materials. The efficient and highly enantioselective synthesis of chiral indole derivatives has become one of the most important issues in organic chemistry. Due to the simple reactivity of the traditional indoles, their involved catalytic asymmetric reactions are very limited, resulting in the limited types of constructed indole-based frameworks. To solve these challenging issues, chemists devised a strategy of introducing simple functional groups to the indole ring, so as to obtain a series of functionalized indole derivatives, namely indole-based platform molecules,as efficient building blocks for constructing chiral indole-related frameworks. Among them, 2-indolylmethanols are a class of important platform molecules, which were designed on the consideration that the introduction of a hydroxymethyl group to C2-position of the indole ring would change the reactivity and the reactive site of the indole ring. This class of platform molecules can act as either electrophiles or nucleophiles, and can act as multi-carbon building blocks in catalytic asymmetric reactions. Therefore, the design and development of 2-indolylmethanols as platform molecules have provided a new strategy for the efficient and highly enantioselective synthesis of chiral indole derivatives. The advances in catalytic asymmetric reactions using 2-indolylmethanols as platform molecules are summarized, which will open a new window for designing and application of new types of indole-based platform molecules.

关 键 词：手性吲哚化学 催化不对称反应 平台分子 吲哚甲醇 

分 类 号：O626[理学—有机化学]