Catalytic hydroacylation: Transforming C-H bonds into biorelevant esters and ketones

催化加氢酰化：将 C-H 键转化为生物相关的酯和酮

• 批准号: 9505179
• 负责人: Vy M Dong
• 金额: $ 9.26万
• 依托单位: UNIVERSITY OF CALIFORNIA-IRVINE
• 依托单位国家: 美国
• 财政年份: 2013
• 资助国家: 美国
• 起止时间: 2013-07-01 至 2018-05-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/9505179
• 关键词: 3-hydroxybutanal; Aldehydes; Alkenes; Alkynes; Amides; Amination; Amines; Antibiotics; Antineoplastic Agents; Biology; Carbon; Catalysis; Cobalt; Complement; Coupling; Development; Emerging Technologies; Esters; Future; Health; Homo; Human; Hydrogen Bonding; Ketones; Knowledge; Lactams; Lactones; Medicine; Metals; Methods; Modernization; Molecular Structure; Natural Products; Nickel; Organic Chemistry; Organic Synthesis; Pharmaceutical Chemistry; Pharmacologic Substance; Reaction; Reagent; Research; Rhodium; Ruthenium; Structure; Time; Ursidae Family; Work; carbonyl group; catalyst; design; diene; drug discovery; ferryl iron; functional group; human disease; innovation; insight; novel; programs; public health relevance; scaffold; tool

DESCRIPTION (provided by applicant): The carbonyl group is a structural motif common in a diverse range of natural products and pharmaceutical agents used to treat human diseases. This project involves the systematic expansion of hydroacylation as an ideal and powerful strategy for making carbonyl-containing compounds, including both esters and ketones. This innovative approach will lead to step- and atom-economical, sustainable, and stereoselective methods that greatly bolster our ability to access molecules relevant to human health, including enantiopure heterocycles and polyketides. In addition, these studies will provide efficient ways to make building blocks that can be elaborated to bioactive structures. Besides the practical value, this project will provide fundamental insights into the use of various catalysts, including rhodium, ruthenium, cobalt, and nickel, for the activation and functionalization of carbon-hydrogen bonds-a long standing challenge in modern organic chemistry.

描述（由申请人提供）：羰基是用于治疗人类疾病的各种天然产物和药剂中常见的结构基序。该项目涉及加氢酰化的系统扩展，作为制造含羰基化合物（包括酯和酮）的理想而强大的策略。这种创新方法将带来步骤和原子经济、可持续和立体选择性的方法，极大地增强我们获取与人类健康相关的分子的能力，包括对映纯杂环和聚酮化合物。此外，这些研究还将提供有效的方法来制造可精细加工为生物活性结构的构件。除了实用价值外，该项目还将提供有关使用各种催化剂（包括铑、钌、钴和镍）来激活和功能化碳氢键的基本见解，这是现代有机化学中长期存在的挑战。

项目成果

Mechanistic insights into hydroacylation with non-chelating aldehydes†Electronic supplementary information (ESI) available: Materials and methods, reaction procedures, characterization data. CCDC 1012849. For ESI and crystallographic data in CIF or other

非螯合醛加氢酰化的机理见解 - 提供电子补充信息 (ESI)：材料和方法、反应程序、表征数据。

• 发表时间: 2015-01-01
• 影响因子: 8.4
• 作者: Murphy, Stephen K;Bruch, Achim;Dong, Vy M
• 通讯作者: Dong, Vy M

Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

铑催化炔烃与二氢吲哚的对映选择性氢胺化。

• 发表时间: 2015-07-08
• 影响因子: 15
• 作者: Chen, Qing;Chen, Zhiwei;Dong, Vy M
• 通讯作者: Dong, Vy M

Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

钴催化下 1,3-二烯的区域选择性加氢酰化。

• 发表时间: 2014-03-12
• 影响因子: 15
• 作者: Chen, Qing;Kim, Daniel K;Dong, Vy M
• 通讯作者: Dong, Vy M

Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis.

串联铑催化：利用亚砜进行不对称过渡金属催化。

• 发表时间: 2015-06-07
• 影响因子: 3.2
• 作者: Kou, K G M;Dong, V M
• 通讯作者: Dong, V M

Rh-Catalyzed Desymmetrization of α-Quaternary Centers by Isomerization-Hydroacylation.

通过异构化-氢酰化作用对 α-四元中心进行 Rh 催化去对称化。

• 发表时间: 2015-08-01
• 影响因子: 8.4
• 作者: Park, Jung;Kou, Kevin G M;Kim, Daniel K;Dong, Vy M
• 通讯作者: Dong, Vy M