1160846-38-7Relevant articles and documents
Catalytic asymmetric iodocyclization of N-tosyl alkenamides using aminoiminophenoxy copper carboxylate: A concise synthesis of chiral 8-oxa-6-azabicyclo[3.2.1]octanes
Arai, Takayoshi,Watanabe, Ohji,Yabe, Shinnosuke,Yamanaka, Masahiro
, p. 12767 - 12771 (2015)
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. An aminoiminophenoxy copper carboxylate-catalyzed asymmetric iodocyclization of N-Tosyl alkenamides gave O-cyclized products in good yields with high enantioselectivity. Chiral 8-oxa-6-azabicyclo[3.2.1]octanes were synthesized by a sequential reduction/cyclization process from the iodocyclization product. DFT calculations suggested that the N-tosyl alkenamides are activated by hydrogen bonding with a carboxylate anion on the copper center to allow iodo-O-cyclization.
