New methods for the asymmetric halogenation of alkenes

烯烃不对称卤化的新方法

• 批准号: 227742917
• 负责人: Professor Dr. Ulrich Hennecke
• 金额: --
• 依托单位: Vakgroep Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2012
• 资助国家: 德国
• 起止时间: 2011-12-31 至 2018-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/227742917?language=en
• 关键词: New; methods; asymmetric; halogenation; alkenes

The addition of halogen electrophiles to the C-C-double bond is one of the most commonly used methods for the functionalisation of alkenes. Even simple non-activated alkenes react with chlorine, bromine and iodine-based electrophiles to give cyclic halonium ions that are opened by a nucleophile in a second step. Although this class of reactions is well known, only a limited number of reagent-controlled asymmetric versions have been described. Especially methods for intermolecular variants such as the dihalogenation of alkenes are missing. Therefore, in this project we develop new procedures for the catalytic asymmetric halofunctionalisation of alkenes based on bifunctional organocatalysts and/or novel chiral conterions.

卤素亲电试剂在C-C双键上的加成是烯烃官能化最常用的方法之一。即使是简单的非活化烯烃与氯，溴和碘基亲电试剂反应，得到环状卤离子，在第二步中被亲核试剂打开。虽然这类反应是众所周知的，只有有限数量的试剂控制的不对称版本已被描述。特别是缺少分子间变体（例如烯烃的二卤代）的方法。因此，在这个项目中，我们开发了基于双官能有机催化剂和/或新型手性离子的烯烃催化不对称卤代官能化的新方法。

项目成果

Synthesis of Chiral Heterocyclic N‐Haloamides and ‐imides and Their Applications as Halogenating Agents and Mechanistic Probes

手性杂环Nâ卤代酰胺和酰亚胺的合成及其作为卤化剂和机理探针的应用

• DOI: 10.1002/ejoc.201601159
• 发表时间: 2017
• 期刊: European Journal of Organic Chemistry
• 影响因子: 2.8
• 作者: U. Hennecke;C. H. Müller;C. G. Daniliuc
• 通讯作者: C. G. Daniliuc

Monomeric Cinchona Alkaloid-Based Catalysts for Highly Enantioselective Bromolactonisation of Alkynes.

• DOI: 10.1002/chem.201604003
• 发表时间: 2016-12
• 期刊: Chemistry
• 作者: M. Wilking;C. Daniliuc;U. Hennecke

Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes.

未官能化烯烃的有机催化、对映选择性二氯化

• DOI: 10.1002/anie.201901777
• 发表时间: 2019
• 期刊: Angewandte Chemie
• 作者: V. Wedek;R. Van Lommel;C. G. Daniliuc;F. De Proft;U. Hennecke
• 通讯作者: U. Hennecke