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Novel bifunctional n-acyliminium ion precursors and their synthetic applications

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A fundamental objective of organic chemistry is the development of selective and efficient synthetic methods. To this end we propose to develop two classes of novel bifunctional reagent. Each contains two sites for carbon carbon bond formation which can be deployed independently and sequentially.
The first class is able to react with two different nucleophiles wherea the second class, a nucleophile and an electrophile. The reactive sites utilise N-acylimminium ion chemistry and palladium catalysed couplings both highly productive bond forming methods. Thus when deployed together they will allow for the efficient construction of an enormous variety of fine chemicals and novel compounds.
We show how such regents can easily be made in enantiomerically pure fo from readily available starting materials. These reagents should prove powerful tools in enantioselective natural product and drug synthesis, and indeed we illustrate this application with several representative examples.

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Universiteit van Amsterdam
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