N-tert-Butylbenzenesulfinimidoyl chloride (
1), developed by Matsuo and Mukaiyama
et al., is an oxidant and is efficiently used for the oxidation of alcohols at room temperature with ease of handling.
1) 1 effectively oxidizes not only typical alcohols but also benzylic and allylic alcohols to aldehydes without complications. Furthermore,
1 is used for the reaction to introduce alkyl groups into the β-position of enones in one pot.
2) In this reaction, the 1,4-addition of alkyl copper reagents to enones successfully proceeds to form the enolate
2, and the subsequent reaction with
1 affords the desired β-alkyl enones via the formation of an intermediate
3. In this way,
1 is easy-to-handle and effective in alcohol oxidations and β-alkyl substitutions of enones, so that it is expected to be widely applied for various organic syntheses such as natural products.