Synthesis of enantiomerically pure funtionalized cis- and trans-2- aminocyclohexanecarboxylic acid derivatives

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10052-10056

  Barluenga, José ^a   Aznar, Fernando ^a   Ribas, Cristina ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANECARBOXYLIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032567289     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981511v     Document Type: Article

References (20)

1. For a review on recent stereoselective synthetic approaches to β-amino acids, see: Cole, D. C. Tetrahedron 1994, 32, 9517-9582.
2. Goto, T.; Toya, Y.; Ohgi, T.; Kondo, T. Tetrahedron Lett. 1982, 23, 1271.
3. Katayama, N.; Nozaki, Y.; Tsubotani, S.; Kondo, M.; Harada, S.; Ono, H. J. Antibiot. 1990, 43, 10.
4. Drey, C. N. C. In Chemistry and Biochemistry of the Amino acids; Barret, G. C., Ed.; Chapman and Hall: New York, 1985; Chapter 3.
5. For the applications of β-amino acids as peptidomimetics, see: Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
6. For a review in the field of β-lactam antibiotics, see: Dürckheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202.
7. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
8. Apella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, Jr. J. J.; Gellman, S. H. Nature 1997, 387, 381-384.
9. Clark, T. D.; Buehler, L. K.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 651-656.
10. (a) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M. P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805-811.
11. (b) Enders, D.; Meyer, O.; Raabe, G. Liebigs Ann. 1996, 1023-1035 and references therein.
12. (a) Barluenga, J.; Aznar, F.; Valdés, C.; Martín, A.; García-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403-4404.
13. (b) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242-1244.
14. (c) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C. J. Org. Chem. 1997, 62, 6746-6753.
15. Spectroscopic data for the alternative approach are included as Supporting Information.
16. Moffett, R. B. Organic Syntheses; Rabjohn, N., Ed.; John Wiley: New York; Collect. Vol. IV, p 1963, 357-359.
17. Osby, J. O.; Ganem, B. Tetrahedron Lett. 1985, 26, 6413-6416.
18. This synthetic study was carried out on racemic 1, obtained by cycloaddition of β-nitrostyrene with the appropriate 2-morpholino-1,3-butadiene.
19. Under the reaction conditions studied, it was not possible to protect exclusively the amino group in the presence of the secondary alcohol, although the monoprotected compound could be isolated with low yields when the reaction was carried out in the presence of smaller amounts of CbzCl.
20. Carlsen, P. H. J.; Katsuki, T.; Martín, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.