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

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 gly...

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Bibliographic Details
Published in:Synthetic communications 2007-05, Vol.37 (10), p.1709-1714
Main Authors: Jursic, Branko S., Sagiraju, Sarada, Ancalade, Dustin K., Clark, Traneil, Stevens, Edwin D.
Format: Article
Language:English
Subjects:
acylaminocinnamic acid
azalactones
azlactone condensation
azlactone ring opening
oxazolones
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910701265895