Oct, 2015
Catalytic Asymmetric Iodocyclization of N-Tosyl Alkenamides using Aminoiminophenoxy Copper Carboxylate: A Concise Synthesis of Chiral 8-Oxa-6-Azabicyclo[3.2.1]octanes
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- ,
- ,
- ,
- Volume
- 54
- Number
- 43
- First page
- 12767
- Last page
- 12771
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1002/anie.201505748
- Publisher
- WILEY-V C H VERLAG GMBH
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.
- Link information
- ID information
-
- DOI : 10.1002/anie.201505748
- ISSN : 1433-7851
- eISSN : 1521-3773
- Web of Science ID : WOS:000363422700047