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The tandem Michael addition – Horner olefination reaction of (S)- alfa-(diethoxyphosphoryl) vinyl p-tolyl sulfoxide was applied for the synthesis of optically active cyclopentenyl sulfoxides, whichwere converted into the corresponding cyclopentenones by Pummerer reaction with trifluroacetic anhydride. The sequence comprising the tandem Michael – Horner reaction, separation of diastereomers and Pummerer reaction afforded enantiomerically pure substituted cyclopentenones.
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Czasopismo
Rocznik
Tom
Strony
211--223
Opis fizyczny
Bibliogr. 19 poz., rys.
Twórcy
autor
autor
autor
autor
- Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, 90-363 Łódź, Sienkiewicza 112, Poland
Bibliografia
- 1. a) Midura W.H., Krysiak J. A., Cypryk M., Mikołajczyk M., Wieczorek M.W. and Filipczak A.D., Eur. J. Org. Chem., 653 (2005) and refereces cited therein; b) Midura W.H., Phosphorus, Sulfur and Silicon, 180, 1285 (2005).
- 2. a) Mikołajczyk M. and Midura W.H., Tetrahedron: Asymmetry, 3, 1515 (1992); b) Mikołajczyk M., Krysiak J., Midura W.H., Wieczorek M.W. and Różycka-Sokołowska E., J. Org. Chem., 71, 8818 (2006).
- 3. a) Trost B.M., Chem. Soc. Rev., 11,141 (1982); b) Collins P.W. and Djuric S.W., Chem. Rev., 93,1533 (1993); c) Zhu G.-D. and Okamura W.H., Chem. Rev., 95, 1877 (1995).
- 4. a) Trost B.M., Li L. and Guille S.D., J. Am. Chem. Soc., 114,8745 (1992); b) Suahara T. and Ogasawara K., Synlett, 419 (1999); c) Boschelli D. and Smith III A.B., Tetrahedron Lett., 22, 3733 (1981);d) Mikołajczyk M., Mikina M. and Żurawiński R., Pure Appl. Chem., 71, 473 (1999).
- 5. a)Scarborough Jr. R.M., Toder B.H. and Smith III A.B., J. Am. Chem. Soc., 102,3904(1980);b) Haneishi T., Kitahara N., Takiguch Y., Aral M. and Sugawara S., J. Antibiot., 27, 386 (1974); c) Jernow J., Tautz W., Rosen P. and Blount J.F., J. Org. Chem., 44, 4210 (1979).
- 6. Grobel B.T. and Seebach D., Synthesis, 357 (1977).
- 7. Hewson A.T., Tetrahedron Lett., 19, 3267 (1978).
- 8. Kennedy M. and McKerve M.A., in Comprehensive Organic Synthesis, B.M. Trost, ed.; Pergamon: Oxford, 1991; Vol. 7, pp. 193-216.
- 9. Craig D., Daniels K. and MacKenzie A.R., Tetrahedron, 49, 11263 (1993).
- 10. Isomerization in similar systems was observed and studied: Trost B.M., Nanninga T.N. and Sato T., J. Am. Chem. Soc., 107, 721 (1985); Goj L.A. and Widenhoefer R.A., J. Am. Chem. Soc., 123, 11133 (2001).
- 11. Under neutral conditions configuration on C3 is stable even at high temperaturę; Hiroi K. and Arinaga Y., Tetrahedron Lett., 35, 153 (1994).
- 12. Conversion of 11 to corresponding cyclopentenone 12 occurs efficiently under Pummerer reaction conditions.
- 13. Buckmelter A.J., Kim A.I. and Rychnovsky S.D., J. Am. Chem. Soc., 122, 9386 (2000).
- 14. KM4CCD software. 2000. Data Collection Program CrysAlis CCD. Version 1.163. UNILIC & KUMA Diffraction Instruments GmbH.
- 15. KM4CCD software. 2000. Data Reduction Program. CrysAlis RED. Version 1.163. UNIL IC & KUMA Diffraction Instruments GmbH.
- 16. Sheldrick G.M., Kruger G.M. and Goddard R., SHELXS-86. Crystallographic Computing 5, Oxford 1985.
- 17. Sheldrick G.M., SHELXL-93. Program for Crystal Structure Refirement, University of Goettingen, Germany, 1993.
- 18. FlackH.D.,Acta Cryst., A39, 876(1983).
- 19. University Chemical Laboratory, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, United Kingdom.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0008-0027