Asymmetric synthesis of α,β-epoxysulfones via phase-transfer catalytic Darzens reaction

Tetrahedron

Volumn 63, Issue 34, 2007, Pages 8099-8103

  Ku, Jin Mo ^a   Yoo, Mi Sook ^a   Park, Hyeung geun ^a   Jew, Sang sup ^a   Jeong, Byeong Seon ^b  

^a Seoul National University   (South Korea)

^b Yeungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZYL DERIVATIVE; BROMINE DERIVATIVE; CINCHONA ALKALOID; SULFONE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; CINCHONA; DARZENS REACTION; ENANTIOSELECTIVITY; PHASE TRANSITION; PRIORITY JOURNAL;

CINCHONA;

EID: 34447107009     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.012     Document Type: Article

References (45)

1. Lauret C., and Roberts S.M. Aldrichimica Acta 35 (2002) 47-51
2. Newman M.S., and Magerlein B.J. Org. React. 5 (1949) 413-441
3. Ballester M. Chem. Rev. 55 (1955) 283-300
4. Berti G. Top. Stereochem. 7 (1973) 93-251
5. Rosen T. Comp. Org. Syn. 2 (1991) 409-439
6. Baldoli C., Buttero P.D., Licandoro E., Maiorana S., and Papagni A. J. Chem. Soc., Chem. Commun. (1987) 762-763
7. Takahashi T., Muraoka M., Capo M., and Koga K. Chem. Pharm. Bull. 43 (1995) 1821-1823
8. Ohkata K., Kimura J., Shinohara Y., Takagi R., and Hiraga Y. Chem. Commun. (1996) 2411-2412
9. Takagi R., Kimura J., Shinohara Y., Ohba Y., Takezono K., Hiraga Y., Kojima S., and Ohkata K. J. Chem. Soc., Perkin Trans. 1 (1998) 689-698
10. Palomo C., Oiarbide M., Sharma A.K., González-Rego M.C., Linden A., García J.M., and González A. J. Org. Chem. 65 (2000) 9007-9012
11. Aggawal V.K., Hynd G., Picoul W., and Vasse J.-L. J. Am. Chem. Soc. 124 (2002) 9964-9965
12. Ghosh A.K., and Kim J.-H. Org. Lett. 6 (2004) 2725-2728
13. Colona S., Fornasier R., and Pfeiffer U. J. Chem. Soc., Perkin Trans. 1 (1978) 8-13
14. Báko P., Szöllosy A., Bombicz P., and Töke L. Synlett (1997) 291-292
15. Báko P., Vizvárdi K., Bajor Z., and Töke L. Chem. Commun. (1998) 1193-1194
16. Báko P., Vizvárdi K., Toppet S., van der Eycken E., Hoornaert G.J., and Töke L. Tetrahedron 54 (1998) 14975-14988
17. Báko P., Czinege E., Báko T., Czugler M., and Töke L. Tetrahedron: Asymmetry 10 (1999) 4539-4551
18. Hummelen J.C., and Wynberg H. Tetrahedron Lett. 19 (1978) 1089-1092
19. Arai S., and Shioiri T. Tetrahedron Lett. 39 (1998) 2145-2148
20. Arai S., Shirai Y., Ishida T., and Shioiri T. Chem. Commun. (1999) 49-50
21. Arai S., Shirai Y., Ishida T., and Shioiri T. Tetrahedron 55 (1999) 6375-6386
22. Arai S., Ishida T., and Shioiri T. Tetrahedron Lett. 39 (1998) 8299-8302
23. Arai S., Ishida T., and Shioiri T. Tetrahedron 58 (2002) 1407-1413
24. For recent books on the phase-transfer catalysis, see:
25. In: Halpern M.E. (Ed). Phase-Transfer Catalysis: Mechanism and Syntheses (1997), American Chemical Society, Washington, DC
26. In: Sasson Y., and Neumann R. (Eds). Handbook of Phase Transfer Catalysis (1997), Blackie A&M, London
27. Shioiri T., and Arai S. In: Vogtle F., Stoddart J.F., and Shibasaki M. (Eds). Stimulating Concepts in Chemistry (2000), Wiley-VCH, Weinheim, Germany 123-143
28. O'Donnell M.J. Catalytic Asymmetric Synthesis. In: Ojima I. (Ed). Asymmetric Phase Transfer Reactions. 2nd ed. (2000), Wiley-VCH, New York, NY Chapter 10
29. In: Berkessel A., and Gröger H. (Eds). Asymmetric Organocatalysis-From Biomimetic Concepts to Applications in Asymmetric Synthesis (2005), Wiley-VCH, Weinheim, Germany
30. Jew S.-s., Jeong B.-S., Yoo M.-S., Huh H., and Park H.-g. Chem. Commun. (2001) 1244-1245
31. Park H.-g., Jeong B.-S., Yoo M.-S., Park M.-k., Huh H., and Jew S.-s. Tetrahedron Lett. 42 (2001) 4645-4648
32. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M.-k., Lee Y.-J., Kim M.-J., and Jew S.-s. Angew. Chem., Int. Ed. 41 (2002) 3036-3038
33. Jew S.-s., Yoo M.-S., Jeong B.-S., Park I.Y., and Park H.-g. Org. Lett. 4 (2002) 4245-4248
34. Jew S.-s., Jeong B.-S., Lee J.-H., Yoo M.-S., Lee Y.-J., Park B.-s., Kim M.G., and Park H.-g. J. Org. Chem. 68 (2003) 4514-4516
35. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park B.-s., Kim M.G., and Jew S.-s. Tetrahedron Lett. 44 (2003) 3497-3500
36. Yoo M.-S., Jeong B.-S., Lee J.-H., Park H.-g., and Jew S.-s. Org. Lett. 7 (2005) 1129-1131
37. In: Simpkins N.S. (Ed). Sulphones in Organic Synthesis. Tetrahedron Organic Chemistry Series Vol. 10 (1993), Pergamon, Oxford
38. Mori Y., Yaegashi K., and Furukawa H. J. Am. Chem. Soc. 118 (1996) 8158-8159
39. Mori Y., Yaegashi K., Iwase K., Yamamori Y., and Furukawa H. Tetrahedron Lett. 37 (1996) 2605-2608
40. Mori Y., Yaegashi K., and Furukawa H. J. Am. Chem. Soc. 119 (1997) 4557-4558
41. Arjona O., Menchaca R., and Plumet J. Tetrahedron 56 (2000) 3901-3907
42. Kita Y., Futamura J., Ohba Y., Sawama Y., Ganesh J.K., and Fujioka H. J. Org. Chem. 68 (2003) 5917-5924
43. Diez D., Beneitez M.T., Marcos I.S., Garrido N.M., Basabe P., Sanz F., Broughton H.B., and Urones J.G. Org. Lett. 5 (2003) 4361-4364
44. Fujioka H., Ohba Y., Futamura J., and Kita Y. Heterocycles 62 (2004) 453-462
45. Diez D., Beneitez M.T., Gil M.J., Moro R.F., Marcos I.S., Garrido N.M., Basabe P., and Urones J.G. Synthesis (2005) 565-568