Efficient diastereo- and enantioselective synthesis of α,β-disubstituted γ-phosphono sulfonates

Tetrahedron Asymmetry

Volumn 20, Issue 21, 2009, Pages 2429-2431

  Enders, Dieter ^a   Mirjafary, Zohreh ^a,b   Saeidian, Hamdollah ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIUM DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; EPIMERIZATION; MICHAEL ADDITION; PRIORITY JOURNAL; PURIFICATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 72149113620     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.011     Document Type: Article

References (35)

1. Enders D., Saint-Dizier A., Lannou M.I., and Lenzen A. Eur. J. Org. Chem. (2006) 29-49
2. Zhang S., Gangal G., and Uludaǧ H. Chem. Soc. Rev. 36 (2007) 507-531
3. Zhou Y.G. Acc. Chem. Res. 40 (2007) 1357-1366
4. Seto H., and Kuzuyama T. Nat. Prod. Rep. 16 (1999) 589-596
5. Fields S.C. Tetrahedron 55 (1999) 12237-12273
6. Kalir A., and Kalir H.H. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Sulfonic Acids, Esters and their Derivatives (1991), Wiley, New York 767-878
7. Morimoto S., Nomura H., Ishiguro T., Fugono T., and Maeda K. J. Med. Chem. 15 (1972) 1105-1108
8. Minami I., Akimoto H., Kondo M., and Nomura H. Chem. Pharm. Bull. 42 (1983) 482-489
9. Dickson J.K., Biller S.A., Magnin D.R., Petrillo Jr. E.W., Hillyer J.W., Hsieh D.C., Lan S., Rinehart J.K., Gregg R.E., Harrity T.W., Jolibois K.G., Kalinoski S.S., Kunselmann L.K., Mookhtiar K.A., and Ciosek Jr. C.P. J. Med. Chem. 39 (1996) 661-664
10. Magnin D.R., Biller S.A., Chen Y., Dickson J.K., Fryszman O.M., Lawrence R.M., Logan J.V.H., Sieber-McMaster E.S., Sulsky R.B., Traeger S.C., Hsieh D.C., Lan S., Rinehart J.K., Harrity T.W., Jolibois K.G., Kunselmann L.K., Rich L.C., Slusarchyk D.A., and Ciosek Jr. C.P. J. Med. Chem. 39 (1996) 657-660
11. For a recent review on the Michael addition to activated vinylphosphonates, see:. Janecki T., Ke{ogonek}dzia J., and Wa{ogonek}sek T. Synthesis (2009) 1227-1254
12. Schick A., Kolter T., Giannis A., and Sandhoff K. Tetrahedron 51 (1995) 11207-11218
13. Enders D., Wahl H., and Papadopoulos K. Tetrahedron 53 (1997) 12961-12978
14. Fernández M.C., Quintela J.M., Ruiz M., and Ojea V. Tetrahedron: Asymmetry 13 (2002) 233-237
15. Fernández M.C., Díaz A., Guillín J.J., Blanco O., Ruiz M., and Ojea V. J. Org. Chem. 71 (2006) 6958-6974
16. Sulzer-Mossé S., Tissot M., and Alexakis A. Org. Lett. 9 (2007) 3749-3752
17. Capuzzi M., Perdicchia D., and Jørgensen K.A. Chem. Eur. J. 14 (2008) 128-135
18. Barros M.T., and Phillips A.M.F. Eur. J. Org. Chem. (2008) 2525-2529
19. Sulzer-Mossé S., Alexakis A., Mareda J., Bollot G., Bernardinelli G., and Filinchuk Y. Chem. Eur. J. 15 (2009) 3204-3220
20. Enders D., Berner O.M., Vignola N., and Bats J.W. Chem. Commun. (2001) 2498-2499
21. Enders D., Vignola N., and Berner O.M. Angew. Chem., Int. Ed. 41 (2002) 109-111 Angew. Chem., Int. Ed. 2002, 114, 116-119
22. Enders D., Berner O.M., Vignola N., and Harnying W. Synthesis (2002) 1945-1952
23. Enders D., Harnying W., and Vignola N. Synlett (2002) 1727-1729
24. Enders D., Harnying W., and Vignola N. Eur. J. Org. Chem. (2003) 3939-3947
25. Enders D., and Harnying W. Synthesis (2004) 2910-2918
26. Enders D., and Harnying W. Arkivoc 2 (2004) 181-188
27. Enders D., Harnying W., and Raabe G. Synthesis (2004) 590-594
28. Enders D., Adelbrecht J.-C., and Harnying W. Synthesis (2005) 2962-2968
29. Enders D., Vignola N., Berner O.M., and Harnying W. Tetrahedron 61 (2005) 3231-3243
30. Harnying W., Kitisriworaphan W., Pohmakotr M., and Enders D. Synlett (2007) 2529-2532
31. Enders D., and Iffland D. Synthesis (2007) 1837-1840
32. Enders D., Iffland D., and Raabe G. Synthesis (2009) 1683-1688
33. Enders D., Saeidian H., Mirjafary Z., Iffland D., Raabe G., and Runsink J. Synlett (2009) 2872-2874
34. For a general review on chiral auxiliaries, see:. Gnas Y., and Glorius F. Synthesis (2006) 1899-1930
35. 2OCO).