Practical Preparation of Z‐α‐(N‐Acetylamino)‐ and Z‐α‐(N‐Benzoylamino)‐α,β‐unsaturated Acids

Abstract

An efficient two‐step synthetic procedure for the preparation of numerous variations of N‐protected α,β‐unsaturated α‐amino acids and their corresponding esters from N‐protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N‐protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base.

Keywords:

• acylaminocinnamic acid
• azlactone condensation
• azlactone ring opening
• azalactones
• oxazolones

Acknowledgment

We express our appreciation to the Louisiana Board of Regents (LEQSF(2001‐04)‐RD‐B‐12) and the National Science Foundation (DMR‐0243977 and EPS‐0092001) for partial support of this work.