Practical Synthesis of Methyl Z-2-(N-Acetylamino) but-2-Enoate. An Intermediate to D- and L-2-Aminobutyric Acid

REFERENCES

• See for example: a) Jackson S. De Grado W. Dwivedi A. Parthasarathy A. Higley A. Krywko J. Rockwell A. Markwalder J. Wells G. Wexler R. Mousa S. Harlow R. J. Am. Chem. Soc. 1994 116 3220
   Web of Science ®Google Scholar
• Jiang , J. , Schumacher , K. K. , Joullie , M. M. , Davis , F. A. and Reddy , R. E. 1994 . Tetrahedron Lett. , 35 : 2121
   Web of Science ®Google Scholar
• Waley , S. G. 1958 . Biochem. J. , 68 : 189
   PubMedGoogle Scholar
• Wilkinson , R. G. , Cantrall , M. B. and Shepherd , R. G. 1962 . J. Med. Chem. , 5 : 835
   Google Scholar
• L-Aspartyl-D-α-aminobutyric acid (S)-α-ethylbenzamide is 2000 times sweeter than sucrose and 5 times as stable as aspartame in beverage applications: Sweeny J. G. D'Angelo L. L. Ricks E. A. Iacobucci G. A. J. Agric. Food Chem. 1995 43 1969
   Web of Science ®Google Scholar
• Burk , M. J. , Feaster , J. E. , Nugent , W. A. and Harlow , R. L. 1993 . J. Am. Chem. Soc. , 115 : 10125 DuPHOS asymmetric hydrogenation technology is available for licensing through Chiroscience, Ltd., Cambridge, U. K
   Web of Science ®Google Scholar
• Srinivasan , A. , Stephenson , R. W. and Olsen , R. K. 1977 . J. Org. Chem. , 42 : 2256
   PubMed Web of Science ®Google Scholar
• Schmidt , U. , Lieberknecht , A. and Wild , J. 1988 . Synthesis , : 159
   Google Scholar
• Balsamini , C. , Duranti , E. , Mariani , L. , Salvatori , A. and Spadoni , G. 1990 . Synthesis , : 779
   Google Scholar
• Andrusziewicz , R. and Czerwinski , A. 1982 . Synthesis , : 968
   Google Scholar
• Somekh , L. and Shanzer , A. 1983 . J. Org. Chem. , 48 : 907
   Google Scholar
• Berti , F. , Ebert , C. and Gardossi , L. 1992 . Tetrahedron Lett. , 33 : 8145
   Google Scholar
• Nugent , W. A. U. S. Patent . 5,559,268 . 1996 .
   Google Scholar
• Srinivasan , A. , Richards , K. D. and Olsen , R. K. 1976 . Tetrahedron Lett. , : 891
   Google Scholar
• Differences in the dehydration of serine and threonine may result from threonine having to adopt a conformation where the methyl group must be syn-periplanar to a large group for elimination to occur thus incurring a substantial non-bonded interaction as the reaction proceeds through the transition state.
   Google Scholar