Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 39, Pages 5456-5459Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801147
Keywords
Palladium; Dehydrogenative; [3+2] Cycloaddition; Tropanes; Asymmetric
Categories
Funding
- National Natural Science Foundation of China (NNSFC) [21672049]
- Hefei University of Technology
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A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition. It allows the generation of structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asymmetric version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.
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