Stereoselective synthesis of (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid

Tetrahedron Asymmetry

Volumn 9, Issue 24, 1998, Pages 4291-4294

  Martín Vilà, Marta ^a   Minguillón, Cristina ^b   Ortuño, Rosa M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; ENZYME MECHANISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0141440727     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00462-5     Document Type: Article

References (21)

1. Boge, T. C.; Georg, G. I.; Tamariz, J. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH, Inc.: New York, 1997; pp. 1 and 45.
2. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
3. Appella, D.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071.
4. Iverson, B. L. Nature 1997, 385, 113.
5. For a recent example on a biologically active peptide including highly substituted β-amino acid residues to restrict the conformational flexibility, see: Hayashi, Y.; Katade, J.; Harada, T.; Tachiki, A.; Iijima, K.; Takiguchi, Y.; Muramatsu, M.; Miyazaki, H.; Asari, T.; Okazaki, T.; Dato, Y.; Yasuda, E.; Yano, M.; Uno, I.; Ojima, I. J. Med. Chem. 1998, 41, 2345.
6. (a) Jiménez, J. M.; Rifé, J.; Ortuño, R. M. Tetrahedron: Asymmetry 1996, 7, 537.
7. (b) Díaz, M.; Ortuño, R. M. Ibid, 1996, 7, 3465.
8. (c) Díaz, M.; Jiménez, J. M.; Ortuño, R. M. Ibid, 1997, 8, 2465.
9. (d) Martín-Vilà, M.; Hanafi, N.; Jiménez, J. M.; Alvarez-Larena, A.; Piniella, J. F.; Branchadell, V.; Oliva, A.; Ortuño, R. M. J. Org. Chem. 1998, 63, 3581.
10. For the synthesis of optically active cyclobutane dehydro α-amino acids from (+)-α-pinene, see: Moglioni, A. G.; García-Expósito, E.; Moltrasio, G. Y.; Ortuño, R. M. Tetrahedron Lett. 1998, 39, 3593.
11. Avotins, F. Russ. Chem. Rev. 1993, 62, 897.
12. Racemic cis-9 had previously been synthesized: Kennewell, P. D.; Mathrau, S. S.; Taylor, J. B.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1, 1982, 2563.
13. Owsley, D.; Bloomfield, J. J. J. Org. Chem. 1971, 36, 3768.
14. Sabbioni, G.; Jones, J. B. J. Org. Chem. 1987, 52, 4565.
15. 2O) δ 25.1, 28.0, 38.9, 41.8, 184.8 (only one set of signals was observed).
16. Isomerization during the Curtius rearrangement has been reported to occur in related systems: (a) Csuk, R.; von Scholz, Y. Tetrahedron, 1994, 50, 10431; (b) Ibid 1995, 51, 7193.
17. Isomerization during the Curtius rearrangement has been reported to occur in related systems: (a) Csuk, R.; von Scholz, Y. Tetrahedron, 1994, 50, 10431; (b) Ibid 1995, 51, 7193.
18. (a) Franco, P.; Minguillón, C.; Oliveros, L. J. Chromatogr. A, 1998, 793, 239.
19. (b) Franco, P.; Senso, A.; Minguillón, C.; Oliveros, L. J. Chromatogr. A, 1998, 796, 265.
20. Columns: 150×4.6 mm, flow rate: 1 ml/min, UV detection: 210 nm.
21. 0