A convenient synthesis of optically active phenylglycine

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 379-380

  Calmes, Monique ^a   Daunis, Jacques ^a   Mai, Nathalie ^a   Natt, François ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PHENYLGLYCINE METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030044776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02170-1     Document Type: Article

References (10)

1. Williams R.M., Organic Chemistry Series Volume 7 : Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989
2. a) Calmes M., Daunis J., Jacquier R., Natt F., Tetrahedron, 1994, 50, 6875;
3. b) Tidwell T., Ketenes, Wiley-Interscience Publication, John Wiley & Sons, New York, 1995, 299 and 642;
4. c) Camps P., Gimenez S., Tetrahedron Asymm., 1995, 6, 991
5. Winter S., Pracejus H., Chem. Ber., 1966, 99, 151
6. Hegedus L.S., Acc. Chem. Res., 1995, 28, 299 and references cited therin
7. Vernier J-M., Hegedus L.S., Miller D.B., J. Org. Chem., 1992, 57, 6914
8. 1H NMR spectrum (Bruker AC 250) by integration of the H-3 signals of the pantolactonyl moiety of the diastereoisomers and by HPLC (column Chirasphere Merck, 25cmx4mm, flow: 1ml/min, hexane/ isopropanol 80/20, retention times : 14.14 min for the S,R isomer and 15.90 min for the R,R isomer).
9. 3.
10. Duhamel L, Fouquay S., Plaquevent J-C., Tetrahedron Lett., 1986, 27, 4975. [α]D= -132 (c=1, MeOH)