Preparation of enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-glyco-4-nitrocyclohex-1-enes

Tetrahedron Asymmetry

Volumn 13, Issue 16, 2002, Pages 1773-1787

  Ballini, R ^a   Bosica, G ^a   Gil, M V ^b   Roman E ^b   Serrano, J A ^b  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5 FORMYL 4 NITROCYCLOHEX 1 ENE; 5 GLYCO 4 NITROCYCLOHEX 1 ENE; ALKENE DERIVATIVE; BASE; CHEMICAL COMPOUND; CYCLOHEXENE DERIVATIVE; FUMARIC ACID DIMETHYL ESTER; MALEIC ACID DERIVATIVE; MALEIC ACID DIMETHYL ESTER; METHYL 4 OXOPENTENOATE; NITROUS ACID; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; DEACETYLATION; ENANTIOMER; MICHAEL ADDITION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037183408     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00416-0     Document Type: Article

References (38)

1. Nitroalkanes and Nitroalkenes in Synthesis. Tetrahedron Symposia-in-print No. 41, Barrett, A. G. M., Ed., Tetrahedron 1990, 6, 7313.
2. Rosini G., Ballini R. Synthesis. 1988;833.
3. Gil M.V., Román E., Serrano J.A. Trends Org. Chem. 9:2001;17.
4. Pham-Huu D.P., Petrusova M., BeMiller J.N., Petrus L. Tetrahedron Lett. 40:1999;3053.
5. Aebischen R., Bieri J.H., Prewo R., Vasella A. Helv. Chim. Acta. 65:1982;2251.
6. D-Alcántara M.P., Escribano F.C., Gómez-Sánchez A., Diánez M.J., Estrada M.D., López-Castro A., Pérez-Garrido S. Synthesis. 1996;64.
7. Drew K.N., Gross P.H. Tetrahedron. 47:1991;6113.
8. Yoshikawa M., Nakae T., Cha B.C., Yokokawa Y., Kitagawa I. Chem. Pharm. Bull. 37:1989;545.
9. Yoshikawa M., Okaichi Y., Cha B.C., Kitagawa I. Tetrahedron. 46:1990;7459.
10. Kitagawa I., Cha B.C., Nakae T., Okaichi Y., Takinami Y., Yoshikawa M. Chem. Pharm. Bull. 37:1989;542.
11. Mahboobi S., Eibler E., Koller M., Kumar S., Popp A., Scholmeyer D. J. Org. Chem. 64:1999;4697.
12. Comoy C., Marot C., Podona T., Baudin M., Morin-Allory L., Guillaumet G., Pfeiffer B., Caignard D., Renard P., Rettori M., Adam G., Guardiola-Lemaître B. J. Med. Chem. 39:1996;4285.
13. Chen Y.J., Chang W.H. J. Org. Chem. 61:1996;2536.
14. Chen Y.J., Wang C.Y., Lin W.Y. Tetrahedron. 52:1996;13181.
15. Latvala A., Stanchev S., Linden A., Hesse M. Tetrahedron: Asymmetry. 4:1993;173.
16. Yamaguchi M., Shiraishi T., Igarashi Y., Hirama M. Tetrahedron Lett. 35:1994;8233.
17. Bakó P., Kiss T., Toke L. Tetrahedron Lett. 38:1997;7259.
18. Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236.
19. Funabashi K., Saida Y., Kanai M., Arai T., Sasai H., Shibasaki M. Tetrahedron Lett. 39:1998;7557.
20. Areces P., Gil M.V., Higes F.J., Román E., Serrano J.A. Tetrahedron Lett. 39:1998;8557.
21. Monosubstituted: methyl acrylate, methyl vinyl ketone, acrylonitrile and acrolein. α,β-Disubstituted: methyl fumarate, methyl maleate, methyl trans-4-oxo-pentenoate and cis-hex-3-en-2,5-dione, unsuccessful attempts were also made with trans-β-nitrostyrene and trans-D-galacto- and -D-manno-1-nitroalkenes.
22. Moreno M.Ch., Plumet J., Román E., Serrano J.A., López M., Ruíz-Pérez C. Tetrahedron Lett. 30:1989;3179.
23. Serrano J.A., Moreno M.Ch., Román E., Arjona O., Plumet J., Jiménez J. J. Chem. Soc., Perkin Trans. 1. 1991;3207.
24. Dominguez C., Csáky A.G., Plumet J. Tetrahedron Lett. 31:1990;7669.
25. Coombes R.G. Comprehensive Organic Chemistry. 2:1979;334 Pergamon Press, New York.
26. Horton D., Wander J.D. J. Org. Chem. 39:1974;1859.
27. Blanc-Muesser M., Defaye J., Horton D. Carbohydr. Res. 87:1980;71.
28. n 1 bond.
29. Ducruix A., Pascard-Billy C., Horton D., Wander J.D. Carbohydr. Res. 29:1973;276.
30. Karplus M. J. Chem. Phys. 30:1959;11.
31. Karplus M. J. Am. Chem. Soc. 30:1963;2870.
32. Eliel E.L. Stereochemistry of Carbon Compounds. 1962;239 McGraw-Hill, New York.
33. Ono N., Kamimura A., Kaji A. J. Org. Chem. 53:1988;251.
34. . This result agrees with previous data about Michael reactions between nitro compounds and α,β-disubstituted olefins: Ballini R., Rinaldi A. Tetrahedron Lett. 35:1994;9247.
35. Gaussian 94 (Revision D.3): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowsky, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andrés, J. L.; Replogle, E. S.; Gomperts, R.; Martín, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; González, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
36. Schwartz A.M., Perry J.W., Bech J. Surface Active Agents and Detergents. 1949;1 Interscience, New York.
37. Schwarzenbach R.P., Gschwend P.M., Imboden D.M. Environmental Organic Chemistry. 1993;Wiley, New York.
38. Piorr R. Structure and Application of Surfactants. Falbe J., Surfactants in Consumer Products. 1987;5-22 Springer, Heildeberg.