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Generation of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones via copper-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes
A new copper-catalyzed three-component annulation–cyanotrifluoromethylation of 1,7-enynes with Togni’s reagent and TMSCN is reproted, and used to produce stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields. [Display omitted] •A new Cu-catalyzed...
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Published in: | Tetrahedron letters 2021-02, Vol.64, p.152722, Article 152722 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | A new copper-catalyzed three-component annulation–cyanotrifluoromethylation of 1,7-enynes with Togni’s reagent and TMSCN is reproted, and used to produce stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields.
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•A new Cu-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes is established.•The mechanism involves a CF3 radical addition-cyclization and radical coupling cascade.•This method provides a new entry for forming stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones.
A new three-component strategy for the copper-catalyzed annulation–cyanotrifluoromethylation of easily available 1,7-enynes with Togni’s reagent and TMSCN is developed. The reaction proceeds smoothly under mild conditions, providing a rapid and concise access to a wide range of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones with a quaternary carbon center in generally good yields. The protocol enjoys wide substrate scope regarding 1,7-enynes, high functional group tolerance and complete stereoselectivity. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2020.152722 |