Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 31, Pages 9226-9230Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201704619
Keywords
[4+3]-cycloaddition; 1,3-bisfunctionalization; cyclopropanes; donor-acceptor compounds; ring-opening reactions
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Funding
- European Research Council (ERC Consolidator Grant GAINBYSTRAIN)
- Studienstiftung des deutschen Volkes
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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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