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Content archived on 2024-06-18

Development of an organic-catalyst mediated cyclopropanation reaction

Objective

A new cyclopropanation reaction will be described, based on ammonium ylides. The reaction of a-chloroketones with electron-deficient alkenes mediated by a nucleophilic tertiary amine will generate the cyclopropane as a single diastereoisomer. The reaction can be performed as a 'one-pot' stoichiometric process, using DABCO as the tertiary amine.

It will be also highly enantioselective under these conditions when a chiral amine is used. Furthermore, the achiral reaction proceeds with a catalytic amount of the tertiary amine providing the first organocatalytic cyclopropanation process. We will also developed an intramolecular version of the reaction that produces fused [n.1.0] bicycloalkanes as a single diastereoisomer.

This intramolecular process for the formation of bicyclic cyclopropanes promises exciting opportunities for applications to the enantioselective synthesis of complex molecules. We will also explore the scope of an asymmetric process with the goal of developing a catalytic enantio-selective intermolecular and intramolecular cyclopropanation reaction, and exploring the use of this process in target synthesis.

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Keywords

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Topic(s)

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Call for proposal

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FP6-2002-MOBILITY-5
See other projects for this call

Funding Scheme

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EIF - Marie Curie actions-Intra-European Fellowships

Coordinator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF CAMBRIDGE
EU contribution
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Total cost

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