Highly stereoselective reduction of acyclic α-sulfinyl ketimines: Synthesis of enantiomerically pure β-aminosulfoxides

Tetrahedron Asymmetry

Volumn 10, Issue 23, 1999, Pages 4607-4618

  García Ruano, José L ^a   Cifuentes, Marta M ^a   Lorente, Antonio ^a   Rodríguez Ramos, Jesús H ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINOSULFOXIDE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; REDUCTION; SPAIN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033367190     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00523-6     Document Type: Article

References (30)

1. See, for example: Bravo, P.; Zanda, P.; Zappala, C. Tetrahedron Lett. 1996, 37, 6005.
2. Bravo, P.; Farina, A.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, P.; Zappala, C. J. Org. Chem. 1997, 62, 3424.
3. Lewanowicz, A.; Lipinski, R.; Siedlecka, R.; Skarzewski, J.; Baert, F. Tetrahedron 1998, 54, 6571.
4. Bravo. P.; Cavicchio, G.; Crucianelli, M.; Pogialli, A.; Zanda, M. Tetrahedron: Asymmetry 1997, 16, 2811.
5. Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixson, C. E.; Grifith, R. J. Org. Chem. 1990, 55, 1086.
6. Rona, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6101.
7. Pyne, S. G.; Dikic, B. J. Org. Chem. 1990, 55, 1932.
8. Bravo, P.; Guidetti, M.; Viani, F.; Zanda, M.; Markovski, A. L.; Sorochinsky, A. E.; Soloshonok, I. V.; Soloshonok, V. A. Tetrahedron 1998, 54, 12789, and references cited therein.
9. Pyne, S. G.; Hajipour, A. R.; Prabakaran, K. Tetrahedron Lett. 1994, 35, 645, and references cited therein.
10. Highly stereoselective processes have recently been reported starting from optically pure N-sulfinyl imines and α-sulfinyl imines (García Ruano, J. L.; Alcudia, A.; Fernández, I.; Barros, D.; Maestro, C. J. Org. Chem. in press) as a result of a double asymmetric induction.
11. Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathy, S. N. J. Org. Chem. 1993, 58, 2144.
12. Hua, D. H.; Bharathy, S. N.; Robinson, P. D.; Tsujimoto, A. J. Org. Chem. 1990, 55, 2128.
13. Hua, D. H.; Bharathy, S. N.; Pananagadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998.
14. Carreño, M. C.; Dominguez, E.; García Ruano, J. L.; Pedregal, C.; Rodriguez J. H. Tetrahedron 1991, 47, 10035.
15. Ogura, K.; Tomori, H.; Fujita, M. Chem. Lett. 1991, 1407.
16. Bravo, P.; Cavicchio, G.; Crucianelly, M.; Markovsky, A. L.; Volonterio, A.; Zanda, M. Synlett 1996, 9, 887, and references cited therein.
17. Navarro, A.; Doctoral PhD Thesis, Valencia, 1999.
18. García Ruano, J. L.; Lorente, A.; Rodriguez J. H. Tetrahedron Lett. 1992, 33, 5637.
19. Hajipoor, A. R. Tetrahedron 1997, 53, 16883.
20. 2 the stereochemical results were slightly lower (see Hua, D. H.; Khiar, N.; Zhang, F.; Lambd, L. Tetrahedron Lett. 1992, 33, 7751).
21. 2 the stereochemical results were slightly lower (see Hua, D. H.; Khiar, N.; Zhang, F.; Lambd, L. Tetrahedron Lett. 1992, 33, 7751).
22. García Ruano, J. L.; Lorente, A.; Rodriguez J. H. Tetrahedron: Asymmetry 1998, 9, 2437.
23. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience: New York, 1999.
24. Carreño, M. C.; García Ruano, J. L.; Martín, A. M.; Pedregal, C.; Rodríguez, J. H.; Rubio, A.; Sánchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120.
25. Park, K. Prakt. Chem. 1912, 86, 287.
26. Brunet, E.; Gallego, M.; García Ruano, J. L.; Alcudia, F. Tetrahedron 1986, 42, 1423.
27. Alcudia, F.; Brunet, E.; García Ruano, J. L.; Hoyos, M. A.; Prados, P.; Rodriguez, J. H. Org. Magn. Resonance 1983, 21, 643.
28. García Ruano, J. L.; Lorente, A.; Rodriguez Ramos, J. H. Tetrahedron Lett. 1998, 39, 9765.
29. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemical, 2nd ed.; Pergamon Press: New York, 1980.
30. See: García Ruano, J. L.; Martín Castro, A. M.; Rodriguez Ramos, J. H. J. Org. Chem. 1992, 57, 7235.