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）：羰基是在多种天然产物和用于治疗人类疾病的药物中常见的结构图案。该项目涉及将水酰化的系统扩展，这是制造含羰基化合物的理想且有力的策略，包括酯和酮。这种创新的方法将导致步骤和原子经济，可持续和立体选择性方法极大地增强了我们访问与人类健康相关的分子的能力，包括对映体杂​​环和聚酮化合物。此外，这些研究将提供有效的方法来制造可以详细说明生物活性结构的基础。除实际价值外，该项目还将提供有关使用各种催化剂的基本见解，包括犀牛，ruthenium，钴和镍，以激活和功能化碳 - 氢键 - 在现代有机化学中长期存在的挑战。

项目成果

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

• DOI: 10.1039/c5sc01553g
• 发表时间: 2015-08-01
• 期刊: Chemical science
• 影响因子: 8.4
• 作者: Park JW;Kou KG;Kim DK;Dong VM
• 通讯作者: Dong VM

Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

• DOI: 10.1002/anie.201410322
• 发表时间: 2015-01-19
• 期刊: Angewandte Chemie (International ed. in English)
• 作者: Whittaker AM;Dong VM
• 通讯作者: Dong VM

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

• DOI: 10.1021/ja500268w
• 发表时间: 2014-03-12
• 期刊: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
• 影响因子: 15
• 作者: Chen, Qing-An;Kim, Daniel K.;Dong, Vy M.
• 通讯作者: Dong, Vy M.

Enantioselective hydroacylation of olefins with rhodium catalysts.

• DOI: 10.1039/c4cc02276a
• 发表时间: 2014-11-18
• 期刊: Chemical communications (Cambridge, England)
• 作者: Murphy SK;Dong VM
• 通讯作者: Dong VM

Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

• DOI: 10.1021/ja512015w
• 发表时间: 2015-03-11
• 期刊: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
• 影响因子: 15
• 作者: Chen, Qing-An;Cruz, Faben A.;Dong, Vy M.
• 通讯作者: Dong, Vy M.