Synthesis of Optically Active δ-Lactones by Rearrangement Reactions
通过重排反应合成光学活性 β-内酯
基本信息
- 批准号:513613124
- 负责人:
- 金额:--
- 依托单位:
- 依托单位国家:德国
- 项目类别:Research Grants
- 财政年份:
- 资助国家:德国
- 起止时间:
- 项目状态:未结题
- 来源:
- 关键词:
项目摘要
Nowadays, the discovery of a new reaction is a very rare event in organic chemistry – and yet it has fortunately happened to us recently. This occasion is the basis for this project: In the presence of a catalytic amount of potassium cyanide 1-hydroxy-2-cyclopentanone carboxylic esters rearrange into δ-valerolactone derivatives. The latter is a prominent structural motif of natural products and synthetic compounds with relevant biological activity. In this project we would like to develop the reaction further into an enantioselective method. We are pursuing two strategies: In a first project, we are planning to control the configuration of the new stereocenter in the product by introducing an additional stereocenter into the starting material. The main and second part of this project, however, is the development of a chiral organocatalyst that allows for an enantioselective transformation to the δ-lactones. On the one hand, it is planned to use cinchona alkaloids to prepare optically active quinuclidinium cyanides and to use them as catalysts. Furthermore, we will investigate chiral ammonium salts as catalysts which are based on the trans-1,2-diaminocyclohexane scaffold. The potential of the new methodology will then be demonstrated in a third project in the stereoselective total synthesis of the natural product chebulic acid and some insect pheromones.
如今,发现一种新反应在有机化学中是非常罕见的事件——然而,幸运的是,它最近发生在我们身上。这个场合是本项目的基础:在催化量的氰化钾存在下,1-羟基-2-环戊酮羧酸酯重新排列成δ-戊内酯衍生物。后者是天然产物和具有相关生物活性的合成化合物的重要结构基序。在这个项目中,我们希望进一步发展该反应成为一种对映选择性方法。我们正在采取两种策略:在第一个项目中,我们计划通过在起始材料中引入额外的立体中心来控制产品中新立体中心的配置。然而,这个项目的主要和第二部分是开发一种手性有机催化剂,允许对映选择性转化为δ-内酯。一方面,计划利用金鸡纳生物碱制备光活性氰化喹啉并作为催化剂。此外,我们将研究手性铵盐作为基于反式-1,2-二氨基环己烷支架的催化剂。新方法的潜力将在第三个项目中得到证明,即天然产物乙酰胆酸和一些昆虫信息素的立体选择性全合成。
项目成果
期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
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Professor Dr. Jens Christoffers其他文献
Professor Dr. Jens Christoffers的其他文献
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{{ truncateString('Professor Dr. Jens Christoffers', 18)}}的其他基金
Polysulfonic acids and polysulfonates: Synthesis, structures, and properties
聚磺酸和聚磺酸盐:合成、结构和性能
- 批准号:
223676145 - 财政年份:2012
- 资助金额:
-- - 项目类别:
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Synthese von Diaminoterephthalsäurederivaten
二氨基对苯二甲酸衍生物的合成
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136068667 - 财政年份:2009
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-- - 项目类别:
Research Grants
Cer-katalysierte, oxidative C-C-Verknüpfungen von 1,3-Dicarbonylverbindungen mit Olefinen und Luftsauerstoff
1,3-二羰基化合物与烯烃和大气氧的铈催化氧化 C-C 键
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5426506 - 财政年份:2004
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Research Grants
Cer-katalysierte alpha-Oxidation von beta-Dicarbonylverbindungen mit molekularem Sauerstoff
铈催化 β-二羰基化合物与分子氧的 α-氧化
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5384227 - 财政年份:2002
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Neue chirale Auxiliare für den Metall-katalysierten Aufbau quartärer Stereozentren
用于金属催化构建四元立构中心的新型手性助剂
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5123204 - 财政年份:1998
- 资助金额:
-- - 项目类别:
Research Grants
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