A general and expeditious route for the preparation of functionalized 2,2-disubstituted 1-nitroalkenes has been developed. Conjugate 1,4-addition of complex zinc cuprates (RCu(CN)ZnI) to easily obtained CE)-l-nitroalkenes, followed by trapping with phenylselenenyl bromide and subsequent oxidative elimination, afforded the corresponding 2,2-disubstituted 1-nitroalkenes in good yields. 2-Alkyl-2-aryl- and 2,2-dialkyl nitroalkenes 4b-g were prepared in 76–88% yield and obtained as E/Z isomeric mixtures, slightly favoring the Z isomer (∼1.0:1.5, E/Z).
ASJC Scopus subject areas
- Organic Chemistry