不对称碳氢官能化构建硅、硼手性及其应用研究

手性现象在自然界中广泛存在，如与生命活动息息相关的生物活性分子DNA、蛋白质、糖类等都与手性密切相关。手性科学在生物医药、材料科学和合成化学等领域扮演着非常重要的角色。天然存在的大多数手性化合物是碳手性化合物，这些碳手性化合物在生命的演化进程中发挥着至关重要的作用。由于手性物质的不同对映异构体对生物体的生理活性不同，因此，合成某一特定构型的化合物对人类的生产生活及生命健康意义重大。

近年来，随着元素有机化学的发展，杂原子手性化合物的构建逐渐成为手性合成化学领域的研究热点。传统获得杂原子手性化合物的方法依赖于使用当量的手性试剂通过手性源合成或利用光学拆分来实现。手性科学在近几十年里得到了快速发展，其中，不对称催化逐渐成为获得手性化合物最直接有效的途径。因此，发展催化不对称方法构建杂原子手性化合物不仅具有重要的理论意义，而且能够为合成化学、材料科学、生物医药等领域提供结构多样的手性化合物。过渡金属催化不对称碳氢键官能化反应具有步骤简洁、效率高、官能团兼容性好等优势，是构建手性分子的有力手段。基于此，本论文在前人研究工作基础之上，利用过渡金属催化不对称碳氢官能化策略，围绕“不对称催化构建硅手性、硼手性化合物及其应用研究”展开。主要内容如下：

在Rh(I)和手性双膦配体催化体系下，利用不对称碳氢硅基化反应成功实现了同时具有硅手性和轴手性的六元环硅烷的高效、高对映选择性构建。该工作通过X-ray单晶衍射的绝对构型分析和Tamao-Fleming氧化实验揭示了一种新颖的硅手性到轴手性传递现象。通过对产物进行衍生化研究，合成了结构新颖的硅醇和具有CPL活性的发光分子。

利用Pd(0)催化不对称碳氢芳基化反应，高效、高对映选择性地实现了一系列硼手性N₂O-BODIPY的构建。该反应成功的关键是在理论计算指导下，设计通过由位阻效应和相互作用力协同调控对映选择性的催化手性口袋配体，精准对映选择性地识别BODIPY中两个吡咯环α位的碳氢键。光学测试研究表明这些化合物具有较好的发光性质，通过对产物进行衍生化可以得到具有红移发射波长的N₂O-BODIPY分子。

基于N₂O-BODIPY化合物的性质特点，从绿色催化角度出发设计合成了一类新型的双功能可见光催化剂，利用低能量的红光作为光源初步探索了其在不对称氧化羟基化反应中的应用。

Chirality exists widely in nature. For example, biological active molecules such as DNA, protein, and sugar, which are closely related to life activities, are closely related to chirality. Chiral science plays a very important role in the fields of biomedicine, material science and synthetic chemistry. Most of the naturally occurring chiral compounds are carbon chiral compounds, which play an important role in the evolution of life. Due to the different enantiomers of chiral substances having different physiological activities for organisms, the synthesis of compounds with a specific configuration is of great significance for human production, life, and health.

In recent years, with the development of element-organic chemistry, the construction of single-configuration heteroatom chiral compounds has gradually become a research hotspot in the field of chiral synthetic chemistry. The traditional method for the preparation of heteroatom stereogenic compounds relies on the use of equivalent chiral reagents through chiral source synthesis or optical resolution. Chiral science has developed rapidly in recent decades, among which asymmetric catalysis has gradually become the most direct and effective way to obtain chiral compounds. Therefore, the development of catalytic asymmetric methods to construct heteroatom stereogenic compounds not only has important theoretical significance, but also can provide chiral compounds with diverse structures for synthetic chemistry, material science, biomedicine, and other fields. Transition metal-catalyzed asymmetric hydrocarbon functionalization has the advantages of simple steps, high efficiency, and good functional group compatibility, which is a powerful means to construct chiral molecules. This thesis builds on the research work of previous researchers, uses the transition metal catalytic asymmetric hydrocarbon functionalization strategy to focus on " asymmetric catalytic construction of silicon chiral, boron chiral compounds and their applications ". The main contents are as follows:

In the presence of a Rh(I) catalyst with a chiral diphosphine ligand, a wide range of dihydrodibenzosilines containing both silicon-central and axial chiralities are conveniently constructed in excellent enantioselectivities via dehydrogenative hydrocarbon silylation. Absolute configuration analysis by single-crystal X-ray structures and Tamao-Fleming oxidation experiment revealed a novel silicon central-to-axial chirality relay phenomenon. Through the derivatization of the product, the silicanol with novel structure and the luminescent molecule with CPL activity were synthesized.

A Pd(0)-catalysed protocol for the enantioselective synthesis of boron-stereogenic N₂O-BODIPYs via hydrocarbon arylation reaction was reported. This method gives access to a wide range of highly functionalized boron-stereogenic N₂O-BODIPYs, including six- to nine-membered boron heterocycles, with good to excellent enantioselectivities. Key to the success of this reaction is to design a catalytic chiral pocket ligand that can precisely and enantioselectively recognize the α C-H bonds of two pyrrole rings in BODIPY by synergistically regulating enantioselectivity through steric hindrance effects and interaction forces under the guidance of theoretical calculations. Photophysical properties, derivatizations of the obtained chiroptical N₂O-BODIPYs are investigated. Optical studies show that these compounds have good luminescence properties; N₂O-BODIPY molecule with red-shift emission wavelength can be obtained by derivatization of the product.

Based on the characteristics of N₂O-BODIPY compound, a new type of bifunctional visible light catalyst was designed and synthesized from the perspective of green catalysis, and its application in asymmetric oxidative hydroxylation was preliminarily explored using low energy red light as the light source.

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