Synthesis of aminocyclohexitol via carbon-carbon bond-forming radical cyclization of oxime ether.
The stannyl radical mediated-cyclization of oxime ether, derived from D-glucose, gave the aminocyclohexitol derivative. Stereoselective C-C bond forming cyclization proceeded via favorable conformers minimizing A(1,3)-strain between the oxime ether group and alpha-substituents.
Miyabe
Hideto
H
Kobe Pharmaceutical University, Kobe, Japan.
Nishiki
Akiyoshi
A
Naito
Takeaki
T
D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis*
D004988:Ethers, Cyclic; D010091:Oximes; D002244:Carbon