Asymmetric epoxidation of 6-cyano-2,2-dimethylchromene on Mn(salen) catalyst immobilized in mesoporous materials

Tetrahedron

Volumn 62, Issue 28, 2006, Pages 6640-6649

  Zhang, Huidong ^a   Li, Can ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Asymmetric epoxidation; Confinement effect; Enantioselective; Heterogeneous chiral catalysis; Mn(salen); Nanopore

Indexed keywords

6 CYANO 2,2 DIMETHYLCHROMENE; CHROMENE DERIVATIVE; MANGANESE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; IMMOBILIZATION; NANOTECHNOLOGY; POROSITY; PRIORITY JOURNAL; SURFACE PROPERTY;

EID: 33744803245     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.117     Document Type: Article

References (65)

1. Blaser H.U., Spindler F., and Studer M. Appl. Catal., A 221 (2001) 119
2. Zhang W., Loebach J.L., Wilson S.R., and Jacobsen E.N. J. Am. Chem. Soc. 112 (1990) 2801
3. Irie R., Noda K., Ito Y., Matsumoto N., and Katsuki T. Tetrahedron Lett. 31 (1990) 7345
4. For recent reviews on heterogeneous chiral catalysis, see:
5. Bianchini C., and Barbaro P. Top. Catal. 19 (2002) 17
6. Fan Q.H., Li Y.M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
7. Song C.-E., and Lee S.-G. Chem. Rev. 102 (2002) 3495
8. Mcmorn P., and Hutchings G.J. Chem. Soc. Rev. 33 (2004) 108
9. Li C. Catal. Rev.-Sci. Eng. 46 (2004) 419
10. Davis M.E. Nature 417 (2002) 813
11. Trong O.D., Desplantier-Giscard D., Danumah C., and Kaliaguine S. Appl. Catal. A 253 (2003) 545
12. Frunza L., Kosslick H., Landmesser H., Hoft E., and Fricke R. J. Mol. Catal. A: Chem 123 (1997) 179
13. Sabatier M.J., Corma A., Domenech A., Fornes V., and Garcia H. Chem. Commun. (1997) 1285
14. Reger T.S., and Janda K.D. J. Am. Chem. Soc. 122 (2000) 6929
15. For covalent grafting of Mn(salen) on mesoporous materials, see:
16. Zhou X.-G., Yu X.-Q., Huang J.-S., Li S.-G., Li L.-S., and Che C.-M. Chem. Commun. (1999) 1789
17. Kim G.-J., and Shin J.-H. Tetrahedron Lett. 40 (1999) 6827
18. Kim G.-J., and Kim S.-H. Catal. Lett. 57 (1999) 139
19. Xiang S., Zhang Y.L., Xin Q., and Li C. Chem. Commun. (2002) 2696
20. Ayala V., Corma A., Iglesias M., Rincón J.A., and Sánchez F. J. Catal. 224 (2004) 170
21. Zhang H.D., Xiang S., and Li C. Chem. Commun. (2005) 1209
22. Zhang H.D., Xiang S., Xiao J.L., and Li C. J. Mol. Catal. A: Chem. 238 (2005) 175
23. Kureshy R.I., Ahmad I., Khan N.H., Abdi S.H.R., Singh S., Pandia P.H., and Jasram R.V. J. Catal. 235 (2005) 28
24. Baleizão C., Gigante B., Garcia H., and Corma A. J. Catal. 221 (2004) 77
25. For ion-exchange of Mn(salen) into layered double hydroxides, see:
26. Fraile J.M., García J.I., Massam J., and Mayoral J.A. J. Mol. Catal. A: Chem. 136 (1998) 47
27. Kureshy R.I., Khan N.H., Abdi S.H.R., Ahmael I., Singh S., and Jasra R.V. J. Catal. 221 (2004) 234
28. Bhattacharjee S., and Anderson J.A. Chem. Commun. (2004) 554
29. Bhattacharjee S., Dines T.J., and Anderson J.A. J. Catal. 225 (2004) 398
30. Piaggio P., Langham C., McMorn P., Bathell D., Page P.C.B., Hancock F.E., Sly C., and Hutchings G.J. J. Chem. Soc., Perkin Trans. 2 (2000) 143
31. Piaggio P., McMorn P., Murphy D., Bathell D., Page P.C.B., Hancock F.E., Sly C., Kerton O.J., and Hutchings G.J. J. Chem. Soc., Perkin Trans. 2 (2000) 2008
32. Schuster C., Möllmann E., Tompos A., and Hölderich W.F. Catal. Lett. 74 (2001) 69
33. Baleizão C., Gigante B., Das D., Alvaro M., Garcia H., and Corma A. Chem. Commun. (2003) 1860
34. Baleizão C., Gigante B., Das D., Alvaro M., Garcia H., and Corma A. J. Catal. 223 (2004) 106
35. Srinivasan K., Michaud P., and Kochi J.K. J. Am. Chem. Soc. 108 (1986) 2309
36. Canali L., Cowan E., Deleuze H., Gibson C.L., and Sherrington D.C. Chem. Commun. (1998) 2561
37. For J. M. Thomas' work about the confinement effect, see:
38. Thomas J.M., Maschmeyer T., Johnson B.F.G., and Shephard D.S. J. Mol. Catal. A: Chem. 141 (1999) 139
39. Jones M.D., Raja R., Thomas J.M., Johnson B.F.G., Lewis D.W., Rouzaud J., and Harris K.D.M. Angew. Chem. Int. Ed. 42 (2003) 4326
40. Raja R., Thomas J.M., Jones M.D., Johnson B.F.G., and Vaughan D.E.W. J. Am. Chem. Soc. 125 (2003) 14982
41. For Hutchings' work about the confinement effect, see:
42. Taylor S., Gullick J., McMorn P., Bethell D., Page P.C.B., Hancock F.E., King F., and Hutchings G.J. J. Chem. Soc., Perkin Trans. 2 (2001) 1714
43. Caplan N.A., Hancock F.E., Page P.C.B., and Hutchings G.J. Angew. Chem. Int. Ed. 43 (2004) 1685
44. Zhang, H. D.; Zhang, Y. M.; Li, C., unpublished.
45. For recent reviews on polymer-immobilized Mn(salen) catalysts, see:
46. Clapham B., Reger T.S., and Janda K.D. Tetrahedron 57 (2001) 4637
47. Dhal P.K., De B.B., and Sivaram S. J. Mol. Catal. A: Chem. 177 (2001) 71
48. Sherrington D.C. Catal. Today 57 (2000) 87
49. Canali L., and Sherrington D.C. Chem. Soc. Rev. 28 (1999) 85
50. Zhang H.D., Zhang Y.M., and Li C. Tetrahedron: Asymmetry 16 (2005) 2417
51. Zhang, H. D.; Zhang, Y. M.; Li, C. J. Catal. 2006, 238, 369.
52. North J.T., Kronenthal D.R., Pullockaran A.J., Real S.D., and Chen H.Y. J. Org. Chem. 60 (1995) 3397
53. Page P.C.B., Buckley B.R., Heaney H., and Blacker A.J. Org. Lett. 7 (2005) 375
54. Lee N.H., Muci A.R., and Jacobsen E.N. Tetrahedron Lett. 32 (1991) 5055
55. For the antihypertensive active compounds with chromene skeleton, see:
56. Cho H., Katoh S., Sayama S., Murakami K., Nakanishi H., Kajimoto Y., Ueno H., Kawasaki H., Aisaka K., and Uchida I. J. Med. Chem. 39 (1996) 3797
57. Bogaert-Alvarez R.J., Demena P., Kodersha G., Polomski R.E., Soundararajan N., and Wang S.S.Y. Org. Process Res. Dev. 5 (2001) 636
58. Bergmann R., Eiermann V., and Gericke R. J. Med. Chem. 33 (1990) 2759
59. For the synthesis of Mn(salen) catalysts, see:
60. Zhang W., and Jacobsen E.N. J. Org. Chem. 56 (1991) 2296
61. Larrow J.F., and Jacobsen E.N. J. Org. Chem. 59 (1994) 1939
62. Hecked A., and Seebach D. Helv. Chim. Acta 85 (2002) 913
63. Bianchi D., Bortolo R., Tassinari R., Ricci M., and Vignola R. Angew. Chem., Int. Ed. 39 (2000) 4321
64. Peng J., Shi F., Gu Y., and Deng Y. Green Chem. 5 (2003) 224
65. Jones C.W., Tsuji K., and Davis M.E. Nature 393 (1998) 52