Ring-Opening 1-Amino-3-aminomethylation of Donor–Acceptor Cyclopropanes via 1,3-Diazepanes |
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| Authors: | M Sc Lennart K B Garve Prof Dr Peter G Jones Prof Dr Daniel B Werz |
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| Institution: | 1. Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany;2. Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany |
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| Abstract: | The first ring-opening reaction of donor–acceptor cyclopropanes to give diamines is reported. For this reaction, a 1,3-bisfunctionalization was developed using cyclopropanes, triazinanes, and Sc(OTf)3 as the catalyst, followed by treatment with acid. The reaction proceeds under very mild conditions and tolerates many functional groups. Moreover, a library of various 1,3-diazepanes, which arise as intermediates of the first formal aza-4+3]-cycloaddition reaction with donor–acceptor cyclopropanes, was synthesized. |
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| Keywords: | [4+3]-cycloaddition 1 3-bisfunctionalization cyclopropanes donor–acceptor compounds ring-opening reactions |
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