Synthesis of chiral β-disulfoxides and their racemization with strong bases

Tetrahedron Asymmetry

Volumn 8, Issue 21, 1997, Pages 3647-3650

  Asensio, Gregorio ^a   Alemán, Pedro A ^a   Medio Simón, Mercedes ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; LIGAND BINDING; METHYLATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON TRANSPORT; RACEMIC MIXTURE;

EID: 0031566719     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00495-3     Document Type: Article

References (11)

1. 1. Kunieda, N., Nokami, J., Kinoshita, M. Bull. Chem. Soc. Jpn 1976, 49, 256.
2. 2. Solladié G., Colobert, F., Ruiz, P., Hamdouchi, C., Carreño, M. C., García Ruano, J. L. Tetrahedron Lett. 1991, 32, 3695.
3. 3. (a) Tokunoh, R., Sodeoka, M., Aoe, K., Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035 and references cited therein;
4. (b) Khiar, N., Fernández, I., Alcudia, F. Tetrahedron Lett. 1993, 34, 123.
5. 4. Satoh, T., Ohara, T., Ueda, Y., Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
6. 5. Although LDA is a hindered base, it reacts with (S)-1 to give the corresponding sulfinimide (Banfi, L., Colombo, L., Gennari, C. Synthesis 1982, 829), which can then react in the same way with disulfoxide 3c.
7. 6. Abbot, D., Colonna, S., Stirling, C. J. M. J. Chem. Soc. Perkin Trans. 1 1976, 492.
8. 7. Posner, G. H., Tang, P.-W., Mallamo, J. P. Tetrahedron Lett. 1978, 3995
9. 8. Furukawa, N., Ogawa, S., Matsumura, K., Fujihara, H. J. Org. Chem. 1991, 56, 6341.
10. 9. Drabowicz, J., Dudzinski, B., Mikolajczik, M. J. Chem. Soc. Chem. Comm. 1992, 1500.
11. 10. Baker, R. W., Hockless, C. R., Pocock, G. R., Sargent, M. V., Shelton, B. W., Sobolev, A. N., Twiss, E., White, A. H. J. Chem. Soc. Perkin Trans. 1 1995, 2615.