1,3-dipolar cycloaddition of diazoalkanes to racemic and optically active α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxides: A new synthesis of 3- phosphorylpyrazoles and asymmetric synthesis of cyclopropanes

Tetrahedron

Volumn 55, Issue 51, 1999, Pages 14791-14802

  Midura, Wanda H ^a   Krysiak, Jerzy A ^a   Mikołajczyk, Marian ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIAZOMETHANE; PYRAZOLE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DECOMPOSITION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTRAL SENSITIVITY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0033579631     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00943-6     Document Type: Article

References (20)

1. (a) Drabowicz, J.; Kiełbasiński, P.; Mikołajczyk, M. in The Synthesis of Sulphones and Sulphoxides and Cyclic Sulphides, Patai, S.; Rappaport, 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.; Rappaport, Z.; Stirling, C.J.M., Eds.; John Wiley and Sons: New York 1998; pp 823-849.
3. (c) Oae, S.; Uchida, Y., ibid.; pp 583-664.
4. Carreño, M.C. Chem. Rev. 1995, 95, 1717-1760.
5. Mikołajczyk, M.; Drabowicz, J.; Kiełbasiński, P.; Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis; CRC Press, Boca Raton, New York, 1997.
6. (a) Mikołajczyk, M.; Midura, W.H., Tetrahedron: Asymmetry, 1992, 3, 1515-1518.
7. (b) Midura, W.H.; Mikołajczyk, M., Phosphorus, Sulfur and Silicon, 1994, 95-96, 395-400.
8. Midura, W.H.; Krysiak, J.A.; Wieczorek, M.W.; Majzner, W.R.; Mikołajczyk, M. Chem. Commun., 1998, 1109-1110.
9. Dean, F.M.; Park, B.K., Tetrahedron Letters, 1974, 4275-4277.
10. Padwa, A.; Meske, M.; Rodriguez, A., Heterocycles, 1995, 40, 191-204.
11. Plancquaert, M.-A.; Redon, M.; Janousek, Z.; Viehe, H.G., Tetrahedron, 1996, 52, 4383-4396.
12. Garcia Ruano, J.L.; Fraile, A.; Martin, R.M., Tetrahedron: Asymmetry, 1996, 7, 1943-1950.
13. The pyrazoles 4b and 5b have been obtained earlier in the reaction of diethyl allenylphosphonate and diazomethane; Pudovik, A.N.; Kchusainova, N.G.; Timoschina, T.W.; Raevskaia, O.E., Z. Obsch. Khim., 1971, 41, 1476-1480.
14. The pyrazole 4d has been obtained earlier in the reaction of diethyl vinylphosphonate and ethyl diazoacetate; Matoba, K.; Yonemoto, H.; Fukui, M.; Yamazaki, T., Chem. Pharm. Bull, 1984, 32, 3918-3925.
15. This part of the present work was preliminary communicated, see ref. 5.
16. For recent papers on the application of this chiral solvating agent see: Drabowicz, J.; Dudziński, B.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1992, 3, 1231-1232; Omelańczuk, J.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1996, 8, 2267-2270; Mikołajczyk, M.; Perlikowska, W.; Omelańczuk, J.; Cristau, H.-J.; Perraud-Darcy, A., J. Org. Chem., 1998, 63, 9716-9722.
17. For recent papers on the application of this chiral solvating agent see: Drabowicz, J.; Dudziński, B.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1992, 3, 1231-1232; Omelańczuk, J.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1996, 8, 2267-2270; Mikołajczyk, M.; Perlikowska, W.; Omelańczuk, J.; Cristau, H.-J.; Perraud-Darcy, A., J. Org. Chem., 1998, 63, 9716-9722.
18. For recent papers on the application of this chiral solvating agent see: Drabowicz, J.; Dudziński, B.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1992, 3, 1231-1232; Omelańczuk, J.; Mikołajczyk, M., Tetrahedron: Asymmetry, 1996, 8, 2267-2270; Mikołajczyk, M.; Perlikowska, W.; Omelańczuk, J.; Cristau, H.-J.; Perraud-Darcy, A., J. Org. Chem., 1998, 63, 9716-9722.
19. All crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre; CCDC 182/835.
20. Engel, P.S., Chem. Rev., 1980, 80, 99-150.