Liquid‐Phase Synthesis of Methyl (E)‐2‐Nitromethyl‐2‐alkenoates Based on PEG‐Supported α‐Phenylselenopropionate

Abstract

The reaction of the lithio derivative of novel polyethylene glycol (PEG)‐supported α‐phenylselenopropionate with aldehydes, followed by oxidation–elimination with 30% hydrogen peroxide and then treatment with sodium nitrite, formed PEG‐bound 2‐nitromethyl‐2‐alkenoates. Subsequent cleavage from the PEG efficiently afforded methyl (E)‐2‐nitromethyl‐2‐alkenoates in good yields and high purities.

Keywords:

• Liquid‐phase organic synthesis
• methyl (E)‐2‐nitromethyl‐2‐alkenoate
• PEG‐supported α‐selenopropionate

Acknowledgments

We gratefully acknowledge financial support from the National Natural Science Foundation (NSF) of China (No. 20562005) and NSF of Jiangxi Province (No. 0620021).