2015年10月
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
- ,
- ,
- ,
- 巻
- 54
- 号
- 43
- 開始ページ
- 12767
- 終了ページ
- 12771
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/anie.201505748
- 出版者・発行元
- 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.
- リンク情報
- ID情報
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- DOI : 10.1002/anie.201505748
- ISSN : 1433-7851
- eISSN : 1521-3773
- Web of Science ID : WOS:000363422700047