General route to racemic and enantiomeric carbo- and heterocyclic vinyl sulfoxides via tandem Michael addition/Horner olefination of α-phosphorylvinyl sulfoxides

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8818-8823

  Mikołajczyk, Marian ^a   Krysiak, Jerzy A ^c   Midura, Wanda H ^a   Wieczorek, Michał W ^b   Rózycka Sokołowska, Ewa ^b  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b JAN DLUGOSZ UNIVERSITY   (Poland)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ISOMERS; NITROGEN COMPOUNDS; OLEFINS; OXYGEN; SYNTHESIS (CHEMICAL);

CARBON NUCLEOPHILIC CENTERS; CYCLOPENTENE SULFOXIDES; HORNER OLEFINATION; MICHAEL ADDITION;

PHOSPHORUS COMPOUNDS;

ALPHA PHOSPHORYLVINYL SULFOXIDE DERIVATIVE; CARBON; CHROMENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN; OXYGEN; PYRROLIZINE DERIVATIVE; QUINOLINE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG; VINYL SULFOXIDE; VINYL SULFOXIDE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; HORNER REACTION; MICHAEL ADDITION; OLEFINATION; ORGANIC CHEMISTRY; RACEMIC MIXTURE; SYNTHESIS;

ALKENES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFOXIDES; VINYL COMPOUNDS;

EID: 33750879888     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061463b     Document Type: Article

References (30)

1. (a) Drabowicz, J.; Kiełbasinski, P.; Mikołajczyk, M. In The Synthesis of Sulfones and Sulfoxides and Cyclic Sulfides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons: New York, 1994; pp 109-388.
2. (b) Posner, G. H. The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons: New York, 1988; pp 823-849.
3. (c) Oae, S.; Uchida, Y. The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons: New York, 1988; pp 583-664.
4. (d) Drabowicz, J.; Kiełbasinski, P.; Mikołajczyk, M. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons: New York, 1988; pp 349-360.
5. Posner, G. M.; Tang, P.-W.; Mallamo, J. P. Tetrahedron Lett. 1978, 42, 3995-3998.
6. Okamura, H.; Mitsuhira, Y.; Miura, M.; Takei, H. Chem. Lett. 1978, 517-520.
7. Carreño, M. C. Chem. Rev. 1995, 95, 7-1760.
8. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339-1367.
9. Mikołajczyk, M.; Drabowicz, J.; Kiełbasinski, P. Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis; CRC Press: Boca Raton, 1997; pp 144-194.
10. Pellissier, H. Tetrahedron 2006, 62, 5559-5601.
11. (a) Abbot, D. J.; Colonna, S.; Stirling, C. J. M. J. Chem. Soc., D 1971, 472-473;
12. Perkin Trans. 1 1976, 492-498.
13. (b) Posner, G. H.; Tang, P. W. J. Org. Chem. 1978, 43, 4131-4136.
14. Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. J. Org. Chem. 1987, 52, 1078-1082.
15. Mikołajczyk, M.; Midura, W. H.; Grzejszczak, S.; Zatorski, A.; Chefczynska, A. J. Org. Chem. 1978, 43, 473-478.
16. Mikołajczyk, M.; Perlikowska, W.; Omelanczuk, J.; Cristau, H.-J.; Perraud-Darcy, A. J. Org. Chem. 1998, 63, 9716-9722.
17. Frye, L. L.; Kogan, T. P.; Mallamo, J. P.; Posner, G. H. Org. Synth. 1985, 64, 196-206.
18. Maezaki, N.; Izumi, M.; Yuyama, S.; Sawamoto, H.; Iwata, Ch.; Tanaka, T. Tetrahedron 2000, 56, 7927-7945.
19. (a) Mikołajczyk, M.; Midura, W. H. Tetrahedron: Asymmetry 1992, 3, 1515-1518.
20. (b) Midura, W. H.; Krysiak, J. A. Tetrahedron 2004, 60, 12217-12229.
21. 16 for details of the preparation of (+)-1b, see Experimental Section of this paper.
22. Midura, W. H.; Mikołajczyk, M. Tetrahedron Lett. 2002, 43, 3061-3065.
23. Flitsch, W.; Lubish, W. Chem. Ber. 1984, 117, 1424-1435.
24. Aromatization of the dihydrochinoline ring by atmospheric oxygen is a well-known process, see, for example: (a) Barton, J. W.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1987, 1541-1545.
25. (b) Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1822-1830.
26. (c) Uno, H.; Okada, S.; Shirashi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 1165-1168.
27. For excellent review on [2,3]-sigmatropic rearrangement of allyl sulfoxides, see: Braverman, S. In The Chemistry of Suphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley and Sons: New York, 1988; pp 717-757.
28. Schweizer, E. E.; Kopay, Ch. M. J. Org. Chem. 1972, 37, 1561-1564.
29. Wender, P. A.; Beckham, S.; Oleary, J. G. Synthesis 1994, 1278-1283;
30. Philips, A. P. J. Am. Chem. Soc. 1946, 68, 2568-2569.