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Remote functionalization by a “deracemizing” metal walk – An innovative approach to define stereochemistry

Project description

The race is on for new methods to achieve remote transformations

Synthetic chemists can run into difficulty when dealing with molecules that can exist in two different physical forms which have the same chemical bonds and atoms, like twisting a part of the molecule without altering which atoms are bonded to each other. Enantiomers, non-superimposable mirror images, are one such class of molecules. They are quite common, and their two forms can have different activities. Achieving so-called enantiomer-pure products is often the goal, and deracemisation is a reaction that can yield a single enantiomer. With the support of the Marie Skłodowska-Curie Actions programme, the DeraceMWalk project is harnessing a novel approach to deracemisation to carry out remote functionalisation that will deliver valuable enantiopure boronic esters.

Objective

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).

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Funding Scheme

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MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)

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Call for proposal

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(opens in new window) H2020-MSCA-IF-2020

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Coordinator

TECHNION RESEARCH AND DEVELOPMENT FOUNDATION LTD
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 173 464,32
Address
THE SENATE BUILDING TECHNION CITY 1
32000 Haifa
Israel

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Activity type
Private for-profit entities (excluding Higher or Secondary Education Establishments)
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 173 464,32
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