Nucleophilic substitution reactions of sulfonyl oxime ether derivatives

Abstract

The nucleophilic substitution reactions of bis-methylsulfonyl methanone O-benzyl oxime and 1-benzenesulfonyl-3-phenyl-propan-1-one O-benzyl-oxime with various nucleophiles were studied. The bis-methylsulfonyl methanone O-benzyl oxime was proven to be a excellent substrate for the nucleophilic substitution reactions. Various nucleophiles including organometallics, enolates, stabilized anions, and heteroatom nucleophiles were reacted with the bis-sulfonyl oxime ether to give the corresponding mono-sulfonyl oxime ethers in good to excellent yields. The 1-benzenesulfonyl-3-phenyl-propan-1-one O-benzyl-oxime was also a very good substrate. It reacted with strong organometallic reagents such as alkyl lithiums and Grignard reagents and with a variety of stabilized anions and deprotonated heteroatom nucleophiles. The sulfonyl group in this substrate performed dual roles of an activation group for the nucleophilic addition reactions and a good leaving group.