Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 11, Pages 2927-2931Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611474
Keywords
[5+4] cycloaddition; heterocycles; homogeneous catalysis; nine-membered rings; palladium
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Funding
- Singapore National Research Foundation [R-143-000-477-281]
- Ministry of Education of Singapore [R-143-000-613-112]
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The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.
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