posted on 2024-01-05, 14:06authored byDiancong Chen, Man Zhang, Dongxu Zhang, Ziqi Zhang, Xusheng Shao, Xiaoyong Xu, Zhong Li, Wu-Lin Yang
The
enantioselective allylic alkylation of nitro ketene aminals
with racemic allylic alcohols was realized by iridium/acid dual catalysis.
An allyl group was installed on the α-position of nitro ketene
aminals in a branched-selective manner in high efficiency with excellent
enantioselectivities (93–99% ee). The protocol was applied
to the late-stage modification of neonicotinoid insecticides, which
directly furnished a novel neonicotinoid analogue with good insecticidal
activity against Aphis craccivora (LC50 = 6.40 mg/L). On the basis of the control experiment, an aza-ene-type
allylic alkylation reaction mechanism was proposed.