H2020Индивидуална стипендия2015–2017

AsymHalogenation · Intermolecular Asymmetric Halogenations of Olefins

„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“

Период: 2015-05-01 → 2017-04-30
Финансиране от ЕС: 185 857 €
Участници: 1
Схема: MSCA-IF-EF-ST

Линиите свързват координатора с партньорите.

Накратко на български

Методи за създаване на специфични форми на халогенирани молекули, подобно на разликата между лява и дясна ръка, са в центъра на работата. Това помага при разработването на лекарства, тъй като само едната форма на молекулата често е активна в организма.

Този кратък обзор е генериран от изкуствен интелект

Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.

Резултати накратко

Intermolecular Asymmetric Halogenations of Olefins

The property of chirality is manifested in both molecular and macroscopic objects. Many organic molecules, including glucose and most biological amino acids, are chiral. This means that they are non-superimposable mirror images of each other, like a left and a right hand are. The two forms of a chiral molecule, called enantiomers, have identical physical and chemical properties, but they interaction with other chiral molecules can be compared with gloves; a left hand interacts differently with left- and right-hand gloves. Therefore, in designing drugs, one must be concerned about which enantiomer is the active one—the one that fits the intended receptor. Ideally, the drug should consist of the pure active isomer. In contrast to the synthesis of biomolecules by organisms where a specific enantiomer is formed, when molecules are synthesized in a laboratory, without using any template, left and right-handed molecules of a compound will form in equal amounts (racemic mixture). Consequently, the development of efﬁcient methods toward the synthesis of chiral compounds is currently of great academic and industrial interest. On the other hand, halogenated natural products are widely distributed in nature. For instance, approximately 5000 compounds known to be produced by living organisms are organohalogens, halogenated natural products. In approximately half of these compounds, the carbon atom to which the halogen is bound is asymmetric. Moreover, incorporation of halogen atoms in drug leads is a common strategy to modify molecules in order to vary their bioactivities and specificities. In view of this, the main goal of this project is the development of a general methodology for the enantioselective synthesis of halogenated molecules having a chiral halonium complex as the source of chirality.

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз

Цел на проекта

The main goal of this project is the development and optimization of the first general methodology for intermolecular asymmetric halogenation of olefins and the application of NMR spectroscopy to understand and control this process. The carefully controlled application of nucleophiles in intermolecular asymmetric halogenation would be extremely desirable because it could be used as a powerful tool to generate a wide array of structural motifs of exceptional impact for the society. In this project, the asymmetric catalysis is proposed by stabilizing a bispyridine halonium complex in a chiral environment during both reaction with the olefin and subsequent attack of the nucleophile, i.e. a stoichiometric amount of stabilized complex will react with the double bond and then be exposed to the incoming nucleophile, all under the regime of the generated chiral environment. Thus, the project will encompass the synthesis of structurally diverse bispyridine ligands and their halonium complexes and then, the elucidation of the influencing factors on the kinetics of the halogenation reaction by UV and NMR spectroscopy. Ultimately, the knowledge gained in this part of the project will be transferred to the design of bispyridine ligands containing asymmetric centers to induce chirality in the halogenation reaction. One or several series of ligands will be produced and screened for chiral induction via chiral HPLC of the product mixture. The applicability of the approach on several different model reactions will be proven. The chiral products should be obtained with a high degree of regio- and enantioselectivity. The bispyridine ligand used to form the stabilized complex can be recovered by extraction or precipitation and therefore its use is expected to be feasible in large scale reactions. Chiral haloalkanes, the products of asymmetric halogenation, are crucial building blocks and intermediates for the synthesis of pharmaceuticals and functional materials, for example.

Оригинален текст от CORDIS (на английски).

Участници

GOETEBORGS UNIVERSITET · GoeteborgКоординаторШвеция