Objective
We wish to develop new asymmetric Brønsted acid catalysed cyclisation reactions that will allow the efficient and highly enantioselective construction of azabicyclic structures from readily available starting materials. This will constitute a new, powerful and broadly applicable organocatalytic asymmetric strategy to such target molecules. Conceptually our proposal is to exploit the high reactivity of N-acyl iminium ions in cyclisation reactions within the asymmetric environment of an associated conjugate base of a chiral Brønsted acid (HA*). For enantioselective N-acyl iminium ion cyclisations, a keto amide starting material with a suitable pi-nucleophile attached to the nitrogen atom of the amide is required. The reaction is technically trivial to perform; a solution of the keto amide starting material is treated with a catalytic quantity of an ‘effective’ chiral Brønsted acid. Loss of water should result in the formation of an N-acyl iminium ion, which, in a low polarity solvent, should be (tight) ion paired with the chiral conjugate base of the Brønsted acid. Provided there is sufficient ordering and effective facial differentiation in the ion pair, attack of the pendant pi-nucleophile will give rise to enantioselectivity in the (irreversible) cyclisation step. During the course of the Fellowship, through physical organic chemistry techniques and molecular modelling calculations we would like to elucidate the mechanistic pathway and origins of stereocontrol in the new catalytic asymmetric methods we are developing. Finally we wish to apply the developed chemistry as a key carbon-carbon bond forming step in the total asymmetric synthesis of an indole alkaloid natural product. Therefore this multidisciplinary Fellowship project will involve the development of innovative asymmetric organic methods, physical organic chemistry, computational chemistry and target synthesis.
Fields of science (EuroSciVoc)
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
CORDIS classifies projects with EuroSciVoc, a multilingual taxonomy of fields of science, through a semi-automatic process based on NLP techniques. See: The European Science Vocabulary.
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Keywords
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Programme(s)
Multi-annual funding programmes that define the EU’s priorities for research and innovation.
Multi-annual funding programmes that define the EU’s priorities for research and innovation.
Topic(s)
Calls for proposals are divided into topics. A topic defines a specific subject or area for which applicants can submit proposals. The description of a topic comprises its specific scope and the expected impact of the funded project.
Calls for proposals are divided into topics. A topic defines a specific subject or area for which applicants can submit proposals. The description of a topic comprises its specific scope and the expected impact of the funded project.
Call for proposal
Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.
Procedure for inviting applicants to submit project proposals, with the aim of receiving EU funding.
FP7-PEOPLE-IIF-2008
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Funding Scheme
Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
Coordinator
OX1 2JD Oxford
United Kingdom
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.