Enantioselective synthesis of α-sulfenylated ketones and aldehydes via α-thiolation of metalated SAMP/RAMP hydrazones

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10239-10252

  Enders, Dieter ^a   Schäfer, Thomas ^a   Mies, Wolfgang ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032572844     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00481-5     Document Type: Article

References (31)

1. 1. Seebach, D.; Teschner, M. Chem. Ber. 1976, 109, 1601-1616.
2. 2. Trost, B. M. Chem. Rev. 1978, 78, 363-382. - Trost, B. M. Acc. Chem. Res. 1978, 11, 453-461.
3. 2. Trost, B. M. Chem. Rev. 1978, 78, 363-382. - Trost, B. M. Acc. Chem. Res. 1978, 11, 453-461.
4. 3. Enders, D.; Piva, O.; Burkamp, F. Tetrahedron 1996, 52, 2893-2908 and literature cited therein.
5. 4. Woo, P. W. K. Tetrahedron 1985, 26, 2973-2976. - Paterson, I.; Alexander, R. P. Tetrahedron Lett. 1985, 27, 5339-5340. - Paterson, I.; Osborne, S. Synlett 1991, 145-146. - Kelly, S. E.; LaCour, T. G. Tetrahedron: Asymmetry 1992, 3, 715-718. - Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1992, 33, 3797-3800.
6. 4. Woo, P. W. K. Tetrahedron 1985, 26, 2973-2976. - Paterson, I.; Alexander, R. P. Tetrahedron Lett. 1985, 27, 5339-5340. - Paterson, I.; Osborne, S. Synlett 1991, 145-146. - Kelly, S. E.; LaCour, T. G. Tetrahedron: Asymmetry 1992, 3, 715-718. - Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1992, 33, 3797-3800.
7. 4. Woo, P. W. K. Tetrahedron 1985, 26, 2973-2976. - Paterson, I.; Alexander, R. P. Tetrahedron Lett. 1985, 27, 5339-5340. - Paterson, I.; Osborne, S. Synlett 1991, 145-146. - Kelly, S. E.; LaCour, T. G. Tetrahedron: Asymmetry 1992, 3, 715-718. - Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1992, 33, 3797-3800.
8. 4. Woo, P. W. K. Tetrahedron 1985, 26, 2973-2976. - Paterson, I.; Alexander, R. P. Tetrahedron Lett. 1985, 27, 5339-5340. - Paterson, I.; Osborne, S. Synlett 1991, 145-146. - Kelly, S. E.; LaCour, T. G. Tetrahedron: Asymmetry 1992, 3, 715-718. - Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1992, 33, 3797-3800.
9. 4. Woo, P. W. K. Tetrahedron 1985, 26, 2973-2976. - Paterson, I.; Alexander, R. P. Tetrahedron Lett. 1985, 27, 5339-5340. - Paterson, I.; Osborne, S. Synlett 1991, 145-146. - Kelly, S. E.; LaCour, T. G. Tetrahedron: Asymmetry 1992, 3, 715-718. - Orena, M.; Porzi, G.; Sandri, S. Tetrahedron Lett. 1992, 33, 3797-3800.
10. 5. Hiroi, K.; Nishida, M.; Nakayama, A.; Nakazawa, K.; Fujii, E.; Sato, S. Chem. Lett. 1979, 969-972. Yura, T.; Iwasawa, N.; Clark, R.; Mukaiyama, T. Chem. Lett. 1986, 1809-1812. - Brunner, H.; Wutz, K.; Doyle, M. P. Monatsh. Chem. 1990, 121, 755-764. - Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165-3168. - Manzoni, L.; Poli, G.; Scolastico, C. Phosphorus, Sulfur and Silicon 1993, 78, 381-382.
11. 5. Hiroi, K.; Nishida, M.; Nakayama, A.; Nakazawa, K.; Fujii, E.; Sato, S. Chem. Lett. 1979, 969-972. Yura, T.; Iwasawa, N.; Clark, R.; Mukaiyama, T. Chem. Lett. 1986, 1809-1812. - Brunner, H.; Wutz, K.; Doyle, M. P. Monatsh. Chem. 1990, 121, 755-764. - Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165-3168. - Manzoni, L.; Poli, G.; Scolastico, C. Phosphorus, Sulfur and Silicon 1993, 78, 381-382.
12. 5. Hiroi, K.; Nishida, M.; Nakayama, A.; Nakazawa, K.; Fujii, E.; Sato, S. Chem. Lett. 1979, 969-972. Yura, T.; Iwasawa, N.; Clark, R.; Mukaiyama, T. Chem. Lett. 1986, 1809-1812. - Brunner, H.; Wutz, K.; Doyle, M. P. Monatsh. Chem. 1990, 121, 755-764. - Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165-3168. - Manzoni, L.; Poli, G.; Scolastico, C. Phosphorus, Sulfur and Silicon 1993, 78, 381-382.
13. 5. Hiroi, K.; Nishida, M.; Nakayama, A.; Nakazawa, K.; Fujii, E.; Sato, S. Chem. Lett. 1979, 969-972. Yura, T.; Iwasawa, N.; Clark, R.; Mukaiyama, T. Chem. Lett. 1986, 1809-1812. - Brunner, H.; Wutz, K.; Doyle, M. P. Monatsh. Chem. 1990, 121, 755-764. - Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165-3168. - Manzoni, L.; Poli, G.; Scolastico, C. Phosphorus, Sulfur and Silicon 1993, 78, 381-382.
14. 5. Hiroi, K.; Nishida, M.; Nakayama, A.; Nakazawa, K.; Fujii, E.; Sato, S. Chem. Lett. 1979, 969-972. Yura, T.; Iwasawa, N.; Clark, R.; Mukaiyama, T. Chem. Lett. 1986, 1809-1812. - Brunner, H.; Wutz, K.; Doyle, M. P. Monatsh. Chem. 1990, 121, 755-764. - Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165-3168. - Manzoni, L.; Poli, G.; Scolastico, C. Phosphorus, Sulfur and Silicon 1993, 78, 381-382.
15. 6. Youn, J. H.; Hermann, R.; Ugi, I. Synthesis 1987, 159-161.
16. 7. Enders, D.; Schäfer, T.; Piva, O.; Zamponi, A. Tetrahedron 1994, 50, 3349-3362.
17. 8. Enders, D.; Zamponi, A.; Schäfer, T.; Nübling, C.; Eichenauer, H.; Demir, A. S.; Raabe, G. Chem. Ber. 1994, 127, 1707-1721.
18. 9. Chibale, K; Warren, S. Tetrahedron Lett. 1994, 35, 3991-3994.
19. 10. Part of the dissertation of Mies, W. University Bonn, 1985 and Schäfer, T. Technical University of Aachen, 1988.
20. 11. Enders, D.; Eichenauer, H. Angew. Chem. 1976, 88, 579-580; Angew. Chem. Int. Ed. Engl. 1976, 15, 549-550. - Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933-2960.
21. 11. Enders, D.; Eichenauer, H. Angew. Chem. 1976, 88, 579-580; Angew. Chem. Int. Ed. Engl. 1976, 15, 549-550. - Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933-2960.
22. 11. Enders, D.; Eichenauer, H. Angew. Chem. 1976, 88, 579-580; Angew. Chem. Int. Ed. Engl. 1976, 15, 549-550. - Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933-2960.
23. 12. For reviews on the SAMP/RAMP hydrazone method see: Enders, D. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press, Orlando, 1984, Vol. 3B, p. 275. - Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Ed.; Wiley, New York, 1995, p. 3368.
24. 12. For reviews on the SAMP/RAMP hydrazone method see: Enders, D. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press, Orlando, 1984, Vol. 3B, p. 275. - Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Ed.; Wiley, New York, 1995, p. 3368.
25. 13. Hesse, W.; Jansen, M. Acta Crystallogr. 1990, C46, 1947-1949.
26. 13C NMR spectroscopy.
27. 3.
28. 16. Correlation of optical rotation.
29. 17. Determined by gaschromatography.
30. 18. Determined by HPLC of the corresponding SASP hydrazone: Enders, D.; Mies, W. J. Chem. Soc. Chem. Comm. 1984, 1221-1223.
31. 19. Determined by GC of the corresponding SASP hydrazone.