Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 43, Pages 12767-12771Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505748
Keywords
asymmetric catalysis; copper; cyclization; DFT calculations; halogenation
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Workshop on Chirality at Chiba University (WCCU)
- Grants-in-Aid for Scientific Research [26105706, 15K05506] Funding Source: KAKEN
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A newly developed aminoiminophenoxy copper carboxylate (L7-Cu-OAc)-catalyzed asymmetric iodocyclization of N-Tosyl alkenamides gave O-cyclized products in good yields with high enantioselectivity. From the O-cyclized products, a skeletal transformation was succeeded in the synthesis of biologically important chiral 8-oxa-6-azabicyclo[3.2.1] octanes. DFT calculations suggested that the acetoxy anion of the [L7-Cu-OAc] acts as a base to generate the anion of N-Tosyl alkenamide substrates. The exchanged acetic acid reconstructs a new hydrogen-bonding network between the catalyst and the substrates to accomplish the highly efficient asymmetric O-iodocyclization of N-Tosyl alkenamides.
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