Zn-mediated catalytic photoreduction of aldimines. One-pot synthesis and separation of meso and d,l C2 symmetrical diamines

Tetrahedron

Volumn 60, Issue 31, 2004, Pages 6475-6478

  Ortega, María ^a   Rodríguez, Miguel A ^a   Campos, Pedro J ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

1,2 Diamines; Imines; Photoreductive coupling; Zinc complexes

Indexed keywords

DIAMINE; IMINE; PHOTOSENSITIZING AGENT; ZINC;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION; PRIORITY JOURNAL; REDUCTION KINETICS; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 4143067286     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.029     Document Type: Article

References (23)

1. Lucet D., Le Gall T., Mioskowski C. Angew. Chem., Int. Ed. Engl. 37:1998;2581
2. Michalson E.T., Szmuskovicz J. Prog. Drug. Res. 33:1989;135
3. Bennani Y.L., Hanessian S. Chem. Rev. 97:1997;3161
4. Annunziata R., Benaglia M., Cinquini M., Caporale M., Raimondi L. Tetrahedron: Asymmetry. 13:2002;2727
5. Hirao T., Hatano B., Imamoto Y., Ogawa A. J. Org. Chem. 64:1999;7665
6. Talukdar S., Banerji A. J. Org. Chem. 63:1998;3468
7. Taniguchi N., Uemura M. Synlett. 1997;51
8. Shimizu M., Iida T., Fujisawa T. Chem. Lett. 1995;609. and references quoted therein
9. Machrouhi F., Namy J.-L., Nief F. Tetrahedron Lett. 40:1999;1315
10. Campos P.J., Caro M., Rodríguez M.A. Tetrahedron Lett. 42:2001;3575
11. Campos P.J., Añón E., Malo M.C., Rodríguez M.A. Tetrahedron. 55:1999;14079
12. Campos P.J., Añón E., Malo M.C., Rodríguez M.A. Tetrahedron. 54:1998;14113
13. Campos P.J., Añón E., Malo M.C., Rodríguez M.A. Tetrahedron. 54:1998;6929
14. Campos P.J., Tan C.-Q., Añón E., Rodríguez M.A. J. Org. Chem. 61:1996;7195
15. Campos P.J., Soldevilla A., Sampedro D., Rodríguez M.A. Org. Lett. 3:2001;4087
16. Campos P.J., Soldevilla A., Sampedro D., Rodríguez M.A. Tetrahedron Lett. 43:2002;8811
17. Campos P.J., Arranz J., Rodríguez M.A. Tetrahedron. 56:2000;7285
18. The presence of triplet quenchers as oxygen inhibited the formation of diamine. In contrast, the presence of a triplet photosensitizer as acetone increased the reaction rate. See Ref. 8
19. In the photoreduction process the solvent act as a source of hydrogen. Solvents without hydrogen donor capability, as tert-butyl alcohol or n-hexane, are ineffective in the photoreaction coupling. See Ref. 8
20. Mimoun H., Yves de Saint Laumer J., Giannini L., Scopelliti R., Floriani C. J. Am. Chem. Soc. 121:1999;6158
21. Photosensitization is a process in which an excited state with the appropriate energy (e.g., a triplet) of one molecular entity (photosensitizer) is deactivated to a lower-lying state by transferring energy to a second molecular entity, which is thereby raised to a higher energy state. See Braslavsky S.E., Houk K.N. Scaiano J.C. Handbook of Organic Photochemistry. Vol. 2:1989;425 CRC, Boca Raton, USA. Chapter 23
22. Mangeney P., Tejero T., Alexakis A., Grosjean F., Normant J. Synthesis. 1988;255
23. Enholm E.J., Forbes D.C., Holub D.P. Synth. Commun. 20:1990;981