Papers

Peer-reviewed
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
  • Takayoshi Arai
  • ,
  • Ohji Watanabe
  • ,
  • Shinnosuke Yabe
  • ,
  • Masahiro Yamanaka

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
DOI
https://doi.org/10.1002/anie.201505748
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000363422700047&DestApp=WOS_CPL
ID information
  • DOI : 10.1002/anie.201505748
  • ISSN : 1433-7851
  • eISSN : 1521-3773
  • Web of Science ID : WOS:000363422700047

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