Stereoselective addition reactions with nitroso derivatives

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On the basis of very successful studies obtained in the first funding period novel stereoselective reactions with nitroso arenes will be established. The novel methods will offer new approaches to important substance classes. Three different stereoselective processes will be addressed. In the first subproject we plan reacting donor-acceptor-cyclopropanes with nitroso arenes in the presence of Lewis acids as catalysts to give enantiomerically pure isoxazolidines in a formal [2+3]-cycloaddition reaction. In addition we will investigate in the second funding period [2+2]-cycloadditions of nitrosoarenes with electron rich alkenes. Along these lines a novel method for the preparation of alpha-aminated lactones will be developed. Finally, the third subproject deals with the reaction of allylboronic acid esters with nitroso arenes for the synthesis of enantiomerically pure allyl alcohols.