A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes

Article abstract of DOI:10.1021/jo00067a016

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 (E)-1-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 76-88percent yield and obtained as E/Z isomeric mixtures, slightly favoring the Z isomer (ca. 1.0:1.5, E/Z).