Radical reaction of oxime ether derivatives

Abstract

The intermolecular addition of alkyl iodides to phenylsulfonyl oxime ether derivatives afforded the aldehydes, ketones, α-keto ester and 1,2-diketone in good yield. The various carbocyclic ketones, and acyclic ketones via sequential radical acylation approach using bis-methylsulfonyl oxime ether were prepared. The radical acylation reaction of O-bensyl-3-iodo-1-methylsulfonyl-propanaldoxime or O-benzyl-4-iodo-1-methylsulfonyl-butanaldoxime with alkene and hexamethylditin afforded α-substituted 5-and 6-membered cyclic ketone in good yield. Radical acylation reaction with alkyne the acylating compounds, so we could obtaine α,β-unsaturated cyclic oxime and protected lactam. All oxime ethers were easily hydrolyzed to the corresponding ketone under acidic condition. Bis-methylsulfonyl oxime ether reacted with various nucleophiles such as: enolates of esters, ketones and α-anions of sulfone. Radical acylation reactions of alkyl iodides with the substituted methylsulfonyl oxime ethers were proceded smoothly, yielding β-keto ester, 1,3-diketone, protected β-keto sulfone and protected lactone through radical acylation reaction.