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Synthesis of amino-cyclobutanes via [2+2] cycloadditions involving keteniminium intermediates

2016    Kolleth, Amandine; Lumbroso, Alexandre; Tanriver, Gamze; Catak, Saron; Sulzer-Mosse, Sarah; De Mesmaeker, Alain

We describe an efficient method for the synthesis of aminocyclobutanes via a [2 + 2] cycloaddition between a keteniminium salt and an alkene, followed by a reduction step. The use of easily removable N-allyl moieties as protecting groups increases the potential of this method to access, in a few steps, highly functionalized cyclobutaneamine-containing building blocks. Moreover, DFT calculations verify the compatibility of N-allyl and N-propargyl keteniminiums in [2 + 2] cycloaddition reactions. (C) 2016 Elsevier Ltd. All rights reserved.