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Synthesis of Functionalized Cyclopentene Derivatives from Vinyldiazo Compounds and Vinylazides through Sequential Copper‐Promoted [3+2] Cycloaddition/Azide Rearrangement
Author(s) -
López Enol,
López Luis A.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201701572
Subject(s) - cyclopentene , azide , cycloaddition , chemistry , diazo , regioselectivity , amine gas treating , allylic rearrangement , copper , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
The reaction of vinylazides with alkenyldiazo compounds in the presence of [Cu(CH 3 CN) 4 ][BF 4 ] provided cyclopentene derivatives with retention of the azide functionality. This process likely involves a sequence comprising: 1) decomposition of the diazo component with generation of a copper alkenylcarbene species; 2) stepwise regioselective [3+2] cycloaddition; 3) allylic azide rearrangement. This method is compatible with a broad range of substrates. We also show that the azide‐containing cycloadducts can be efficiently converted into the corresponding amine and triazole derivatives.