Reaction of Functionalized Carbodiimide with α-Amino Ester: A Selective Synthesis of 2,3,5-Trisubstituted Imidazol-4-ones

Abstract

3-(Ethoxycarbonylmethylene)-2-(arylimino)-imidazol-4-ones 5 were synthesized selectively by reaction of α-amino ester with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphoranes 2 with aromatic isocyanates.

Keywords:

• α-Amino ester
• aza-Wittig reaction
• carbodiimide
• imidazolin-4-one
• ylides

ACKNOWLEDGMENT

We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 20772041) and Hubei Province (No. 2006ABB016) and the Key Project of Chinese Ministry of Education (No. 107082).

Notes

^a Isolated yields based on carbodiimide 3.

^b The ee was determined by HPLC.