DeraceMWalk · Remote functionalization by a “deracemizing” metal walk – An innovative approach to define stereochemistry
„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“
- Период
- 2021-05-11 → 2023-05-10
- Финансиране от ЕС
- 173 464 €
- Участници
- 1
- Схема
- MSCA-IF
Линиите свързват координатора с партньорите.
Накратко на български
Метални катализатори ще се използват за пренареждане на атомите в разклонени въглеродни вериги, за да се контролира тяхната пространствена структура. Това помага за по-лесното създаване на сложни молекули с точно определена форма.
Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.
Резултати накратко
Remote functionalization by a “deracemizing” metal walk – An innovative approach to define stereochemistry
This project seeks to investigate a completely different approach in the field of remote functionalization. We are now proposing to create stereocenters during the metal-walk by “deracemization” of branched substituents, a process that yet remains an unknown terrain. Although this is a high-risk project, we believe that the expertise acquired in this field should allow the design of a proper system that would combine a triggering event at the initiation site followed by a “deracemizing” metal-walk process along the hydrocarbon chain through the induction of a metal/chiral ligand system. This corrective metal walk should induce specific stereochemistry of (multiple) sp3 carbon centers along a branched alkyl chain. Subsequently, functionalization at the terminal position will be addressed. This approach will consist of three major events: (i) a functionalization at the initiation site distal from the remote site; (ii) a “deracemization” metal-walk processes that should determine the stereochemistry of the branched stereocenters and (iii) a termination step at the remote site. This technology will lead to the foundation of new developments in one of the most vibrant areas of expertise when building up molecular complexity and open new vistas in chain-walking scenarios, and in particular within the context of remote functionalization. In this respect, the proposed project aims to merge the fundamentals of a remote functionalization, namely a remote metal-catalyzed hydroboration reaction and a novel “deracemizing” metal-walk that will control the stereochemistry while passing branched alkyl chains. Thus, besides a careful choice of a suitable metal source, catalyst design will be crucial and might involve design and evaluation of novel ligands. This approach offers then an entry to a diastereo- and enantioselective synthesis of complex acyclic architectures including (multiple) stereocenters that otherwise might not be accessible.
Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз
Цел на проекта
In conclusion this proposal nicely combines a study of a Co-catalyzed remote hydroboration with a modern and conceptionally new approach to define stereochemistry through an elegant “deracemization” process mediated by a metal/ligand catalyst. Through this method, branched alkyl chains en route to highly complex scaffolds with a well-defined stereochemistry should be accessible. This strategy will be an invaluable asset to the scarcely existing methods creating multiple stereogenic centers in only one transformation (one could prepare 1,n-stereocenters through this approach). Moreover, the anticipated remote functionalization delivers valuable enantiopure boronic esters, that might serve as interesting and important intermediates in natural product synthesis and medical chemistry. Furthermore, mechanistic studies will give a better understanding of the proposed transformation and may pave the way for further remote transformations that involve a deracemizing metal-walk possessing branched alkyl chains (e.g. remote hydrosilylation).
Оригинален текст от CORDIS (на английски).
Участници
- TECHNION RESEARCH AND DEVELOPMENT FOUNDATION LTD · HaifaКоординаторИзраел
Връзки
Данни: CORDIS, © Европейски съюз