Horner-Wadsworth-Emmons reaction for the synthesis of unusual α,β-didehydroamino acids with a chiral axis

Arkivoc

Volumn 2004, Issue 4, 2004, Pages 59-66

  Cativiela, Carlos ^a   Díaz De Villegas, María D ^a   Gálvez, José A ^a   Su, Guifa ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b GUANGXI NORMAL UNIVERSITY   (China)

Author keywords

Amino acids; Olefination

Indexed keywords

2 (N BENZYLOXYCARBONYLPHENYLALANYLAMINO)ACETIC ACID METHYL ESTER DERIVATIVE; 2 BENZYLOXYCARBONYLAMINOACETIC ACID METHYL ESTER DERIVATIVE; ACETIC ACID ESTER; ALPHA,BETA DIDEHYDROAMINO ACID; AMINO ACID DERIVATIVE; GLYCINE DERIVATIVE; N BENZYLOXYCARBONYL(DIMETHYLPHOSPHINYL)GLYCINE; PHENYLALANINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; HORNER WADSWORTH EMMONS REACTION; HYDROGENOLYSIS; PEPTIDE SYNTHESIS; RACEMIC MIXTURE; REACTION ANALYSIS;

EID: 2942635882     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. For reviews on this subject see: a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172.
2. b) Smith, M. J.; Kim, D.; Horenstein, B.; Nakanishi, K.; Kustin, K. Acc. Chem. Res. 1991, 24, 117-124.
3. a) Gross, L. M.; Morell, P. M.; Craig, G. T. Proc. Natl. Acad. Sci. USA 1969, 62, 953-961.
4. b) Stammer, C. H. Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, B. Weinstein Ed., Marcel Dekker: New York, 1982, Vol. 6, pp 33-74.
5. c) Aydin, M.; Lucht, N.; Koenig, W. A.; Lupp, R.; Jung, G.; Winkelmann, G. Liebigs Ann. Chem. 1985, 2285-2300.
6. d) Fate, G. D.; Benner, C. P.; Grode, S. H.; Gilbertson, T. J. J. Am. Chem. Soc. 1996, 118, 11363-11368.
7. a) Shimohigashi, Y.; Stammer, C. H.; Costa, T.; von Voigtlander, P. F. Int. J. Pept. Protein Res. 1983, 22, 489-494.
8. b) Brady, S. F.; Cochran, D. W.; Nutt, R. F.; Holly, F. W.; Bennett, C. D.; Paleveda, W. J.; Curley, P. E.; Arison, B. H.; Saperstein, R.; Weber, D. Int. J. Pept. Protein Res. 1984, 23, 212-222.
9. c) Salvadori, S.; Marastoni, M.; Balboni, G.; Marzola, G.; Tomatis, R. Int. J. Pept. Protein Res.1986, 28, 254-261.
10. d) Salvadori, S.; Marastoni, M.; Balboni, G.; Marzola, G.; Tomatis, R. Int. J. Pept. Protein Res. 1986, 28, 262-273.
11. e) Imazu, S.; Shimohigashi, Y.; Kodama, H.; Sakaguchi, K.; Waki, M.; Kato, T.; Izumiya, N. Int. J. Pept. Protein Res. 1988, 32, 298-306.
12. Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron Lett. 1999, 40, 1027-1030.
13. Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563-580.
14. a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-60.
15. Schmidt, U.; Grieser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
16. b) Park, K. C.; Yoshino, K.; Tomiyasu, H.; Synthesis 1999, 2041-2044.