SusChEM: Design of Organocatalysts through Computational Screening

SusChEM：通过计算筛选设计有机催化剂

基本信息

批准号：
1665407
负责人：
Steven Wheeler
金额：
$ 35.89万
依托单位：
University of Georgia Research Foundation Inc
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2017
资助国家：
美国
起止时间：
2017-07-15 至 2021-06-30
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1665407&HistoricalAwards=false
关键词：
SusChEM Design Organocatalysts through Computational

项目摘要

The Chemical Catalysis Program of the Chemistry Division supports the project by Professor Steven E. Wheeler. Professor Wheeler is a faculty member in the Center for Computational Quantum Chemistry, Department of Chemistry at the University of Georgia. He is developing a free, open-source computational toolkit (AARON) to facilitate the design of transition-metal free asymmetric catalysts. This toolkit is being implemented to help develop new catalysts with applications in the synthesis of complex natural products and pharmaceuticals. This project will make it easier for non-specialists to use computational chemistry to design and evaluate new organocatalysts. The primary goal of this project is to provide computational tools that reduce the time and materials required to design new catalysts, thereby streamlining the catalyst design process. The project combines ideas from computational quantum chemistry, software development, data analytics, and organic synthesis, and provides graduate and undergraduate students with diverse training in highly transferrable skills. The project also supports a workshop on computational organic chemistry that is held in conjunction with an annual undergraduate computational chemistry conference organized by the MERCURY consortium.The development of new asymmetric organocatalysts typically depends on the experimental screening of a library of potential catalysts to identify the best catalysts for a single substrate. The substrate scope of this catalyst is then tested. The AARON program provides an alternative path for the development of organocatalysts with broad substrate scope by enabling the automated computational screening of virtual libraries of catalysts applied to multiple substrates simultaneously. In this way, the synthesis and testing of new catalysts can be prioritized based on predicted stereoselectivities and catalytic activities across a range of substrates. AARON is designed to identify novel bifunctional hydrogen bonding catalysts and chiral phosphoric acids for several reactions and to unravel the origin of stereoselectivity in ion-pairing catalysis. The development of an accompanying graphical interface for AARON enable its widespread use among organic chemists, while an online public database provides access to transition state structures, energies, and stereoselectivities, facilitating the application of modern data analysis tools to these rich datasets. Educational activities include the training of undergraduate and graduate students in computer programming, advanced electronic structure theory, and physical organic chemistry. Outreach activities include the development of a computational organic chemistry workshop for undergraduates, and the training of students in modern data analytics through the Georgia Informatics Institutes (GII).

化学部的化学催化计划由史蒂文·E·惠勒（Steven E. Wheeler）教授支持该项目。惠勒教授是佐治亚大学化学系计算量子化学中心的教职员工。他正在开发一个免费的开源计算工具包（AARON），以促进过渡金属不对称催化剂的设计。正在实施该工具包，以帮助开发新的催化剂，并在合成复杂的天然产品和药品中应用。该项目将使非专家更容易使用计算化学设计和评估新的有机催化剂。该项目的主要目标是提供计算工具，以减少设计新催化剂所需的时间和材料，从而简化催化剂设计过程。该项目结合了计算量子化学，软件开发，数据分析和有机综合的想法，并为研究生和本科生提供了高度可转移技能的多种培训。该项目还支持有关计算有机化学的研讨会，该研讨会与汞财团组织的年度本科计算化学会议结合在一起。新的不对称有机催化剂的开发通常取决于对潜在催化剂的实验性筛选，以识别单个副催化剂的最佳催化剂。然后测试该催化剂的底物范围。 AARON计划通过启用对催化剂的虚拟库的自动计算筛选，同时应用于多个底物的催化剂的虚拟库，从而为具有广泛的底物范围的有机催化剂提供了替代途径。通过这种方式，可以根据预测的立体选择性和各种底物的催化活性来优先考虑新催化剂的合成和测试。 Aaron旨在鉴定新型的双功能氢键催化剂和手性磷酸，用于几种反应，并揭示离子配对催化中立体选择性的起源。 Aaron随附的图形接口的开发使其在有机化学家中广泛使用，而在线公共数据库则可以访问过渡状态结构，能量和立体选择性，从而促进了现代数据分析工具在这些富数据集中的应用。教育活动包括在计算机编程，高级电子结构理论和物理有机化学方面的本科和研究生培训。外展活动包括开发针对本科生的计算有机化学研讨会，以及通过佐治亚州信息学院（GII）在现代数据分析中培训学生。

项目成果

期刊论文数量（12）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Automated Quantum Mechanical Predictions of Enantioselectivity in a Rhodium-Catalyzed Asymmetric Hydrogenation

DOI：
10.1002/anie.201704663
发表时间：
2017-07-24
期刊：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
影响因子：
16.6
作者：
Guan, Yanfei;Wheeler, Steven E.
通讯作者：
Wheeler, Steven E.

Importance of Electrostatic Effects in the Stereoselectivity of NHC-Catalyzed Kinetic Resolutions

DOI：
10.1021/jacs.7b01796
发表时间：
2017-09-13
期刊：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
影响因子：
15
作者：
Maji, Rajat;Wheeler, Steven E.
通讯作者：
Wheeler, Steven E.

Importance of favourable non-covalent contacts in the stereoselective synthesis of tetrasubstituted chromanones

有利的非共价接触在四取代色满酮立体选择性合成中的重要性

DOI：
10.1039/d2qo00090c
发表时间：
2022
期刊：
Organic Chemistry Frontiers
影响因子：
5.4
作者：
Andreola, Laura R.;Wheeler, Steven E.
通讯作者：
Wheeler, Steven E.

Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane

烯基三氯硅烷醛不对称炔丙基化催化剂结构优化

DOI：
10.1002/adsc.202000936
发表时间：
2020
期刊：
Advanced Synthesis & Catalysis
影响因子：
5.4
作者：
Vaganov, Vladimir Yu.;Fukazawa, Yasuaki;Kondratyev, Nikolay S.;Shipilovskikh, Sergei A.;Wheeler, Steven E.;Rubtsov, Aleksandr E.;Malkov, Andrei V.
通讯作者：
Malkov, Andrei V.

Modulating Stereoselectivity through Electrostatic Interactions in a SPINOL-Phosphoric Acid-Catalyzed Synthesis of 2,3-Dihydroquinazolinones