Efficient dual catalytic enantioselective diethylzinc addition to the exocyclic C{double bond, long}N double bond of some 1,2,4-N-triazinylarylimines using polymer-supported chiral β-amino alcohols derived from norephedrine

Tetrahedron

Volumn 63, Issue 25, 2007, Pages 5490-5500

  El Shehawy, Ashraf A ^a  

^a Kafr El Sheikh University   (Egypt)

Author keywords

1,2,4 Triazines; Arylimines; Chiral polymers; Dual catalytic; Enantioselective ethylation; Lewis acids; Polymeric reagents and catalysts

Indexed keywords

AMINOALCOHOL; AROMATIC AMINE; BETA AMINOALCOHOL; CARBON; CARBONYL DERIVATIVE; COPOLYMER; DIETHYLZINC; EXOCYCLIC DOUBLE BOND; IMINE; NOREPHEDRINE; POLYMER; THIOL DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; LOW TEMPERATURE; PRIORITY JOURNAL;

EID: 34248513143     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.04.041     Document Type: Article

References (97)

1. Gravert D.J., and Janda K.D. Chem. Rev. 97 (1997) 489
2. Pu L. Tetrahedron: Asymmetry 9 (1998) 1457
3. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. I-III (1999), Springer, Berlin
4. In: Ertl G., Knözinger H., and Weitkamp J. (Eds). Preparation of Solid Catalysts (1999), Wiley-VCH, Weinheim
5. Astruc D., and Chardac F. Chem. Rev. 101 (2001) 2991
6. Clapham B., Reger T.S., and Janada K.D. Tetrahedron 57 (2001) 4637
7. Rechavi D., and Lemaire M. Chem. Rev. 102 (2002) 3467
8. Benaglia M., Puglisi A., and Cozzi F. Chem. Rev. 103 (2003) 3401
9. Bräse S., Lauterwasser F., and Ziegert R.E. Adv. Synth. Catal. 345 (2003) 869
10. McMorn P., and Hutchings G.J. Chem. Soc. Rev. 33 (2004) 108
11. Palomo C., Oiarbide M., and García J.M. Chem. Soc. Rev. 33 (2004) 65
12. Chung C.W.Y., and Toy P.H. Tetrahedron: Asymmetry 15 (2004) 387
13. Itsuno S. Prog. Polym. Sci. 30 (2005) 540
14. El-Shehawy A.A., and Itsuno S. Preparation of Immobilized Chiral Ligands onto Polymer Supports and their Application to Asymmetric Synthesis. In: Bregg R.K. (Ed). Current Topics in Polymer Research (2005), Nova Science, New York, NY 1
15. Hanson B.E. In: De Vos D.E., Vankelecom I.F.J., and Jacobs P.A. (Eds). Chiral Catalyst Immobilization and Recycling (2000), Wiley-VCH, Weinheim 81
16. In: Nicolaou K.C., Hanko R., and Hartwig W. (Eds). Handbook of Combinatorial Chemistry, Drugs, Catalysts, Materials (2002), Wiley-VCH, Weinheim
17. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
18. McNamara C.A., Dixon M.J., and Bradley M. Chem. Rev. 102 (2002) 3275
19. Jönsson C., Hallman K., Andersson H., Stemme G., Malkoch M., Malmström E., Hult A., and Moberg C. Bioorg. Med. Chem. Lett. 12 (2002) 1857
20. Luis S.V., Altava B., Burguete M.I., Collado M., Escorihuela J., García-Verdugo E., Vicent M.J., and Martens J. Ind. Eng. Chem. Res. 42 (2003) 5977
21. Liu P.N., Gu P.M., Wang F., and Tu Y.Q. Org. Lett. 6 (2004) 169
22. Denmark S.E., and Nicaise O.J.-C. Chem. Commun. (1996) 999
23. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895
24. Federsel H.-J., Collins A.N., Sheldrake G.N., and Crosby J. Chirality Industry II (1997), John Wiley and Sons, Chichester, UK p 225
25. Bloch R. Chem. Rev. 98 (1998) 1407
26. Denamrk S.E., and Nizaise O.J.-C. In: Jacobson E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, Berlin 923
27. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
28. Côté A., and Charete A.B. J. Org. Chem. 70 (2005) 10864
29. Chelucci G. Tetrahedron: Asymmetry 16 (2005) 2353
30. Itsuno S., Watanabe K., Ito K., El-Shehawy A.A., and Sarhan A.A. Angew. Chem., Int. Ed. 36 (1997) 109
31. El-Shehawy A.A., Abdelaal M.Y., Watanabe K., Ito K., and Itsuno S. Tetrahedron: Asymmetry 8 (1997) 1731
32. Itsuno S., Watanabe K., Matsumoto T., Kuroda S., Yokoi A., and El-Shehawy A. J. Chem. Soc., Perkin Trans. 1 (1999) 2011
33. Itsuno S., Watanabe K., and El-Shehawy A.A. Adv. Synth. Catal. 343 (2001) 89
34. El-Shehawy A.A., Omara M.A., Ito K., and Itsuno S. Synlett (1998) 367
35. Itsuno S., El-Shehawy A.A., Abdelaal M.Y., and Ito K. New J. Chem. (1998) 775
36. Itsuno S., and El-Shehawy A.A. Polym. Adv. Technol. 12 (2001) 670
37. Pinho P., and Anderson P.G. Tetrahedron 57 (2001) 1615
38. Zhang X., Gong L., Mi A., Cui X., Jiang Y., Choi M.C.K., and Chan A.S.C. Tetrahedron Lett. 42 (2001) 6369
39. Zhang X., Lin W., Gong L., Mi A., Cui A., Jiang A., Choi M.C.K., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 1535
40. Bertrand M., Feray L., and Gastaldi S. C.R. Chimie 5 (2002) 623
41. Zhang H.-L., Zhang X.-M., Gong L.-Z., Mi A.-Q., Cui X., Jiang Y.-Z., Choi M.C.K., and Chan A.S.C. Org. Lett. 4 (2002) 1399
42. Liu H., Zhang H.-L., Wang S.-J., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Tetrahedron: Asymmetry 16 (2005) 2901
43. Lauzon C., and Charette A.B. Org. Lett. 8 (2006) 2743
44. Basra S., Fennie M., and Kozlowski M. Org. Lett. 8 (2006) 2659
45. Hayashi T., and Ishigedani M. J. Am. Chem. Soc. 122 (2000) 976
46. Fujihara H., Nagai K., and Tomioka K. J. Am. Chem. Soc. 122 (2000) 12055
47. Sato I., Kodaka R., and Soai K. J. Am. Chem. Soc., Perkin Trans. 1 (2001) 2919
48. Hermanns N., Dahmen S., Blom C., and Bràse S. Angew. Chem., Int. Ed. 41 (2002) 3692
49. Hayashi T., and Ishigedani M. Tetrahedron 57 (2002) 2589
50. Dahmen S., and Bràse S. J. Am. Chem. Soc. 124 (2002) 5940
51. Boezio A.A., and Charette A.B. J. Am. Chem. Soc. 125 (2003) 1692
52. Li X., Cun L.-Z., Mi A.-Q., and Jiang Y.-Z. Tetrahedron: Asymmetry 14 (2003) 3819
53. Soeta T., Nagai K., Fujihara H., and Kuriyama M. J. Org. Chem. 68 (2003) 9723
54. Zhang H.-L., Jiang F., Zhang X.-M., Gong L.-Z., Mi A.-Q., Cui X., Jiang Y.-Z., and Wu Y.-D. Chem.-Eur. J. 10 (2004) 1481
55. Tokunaga N., Otomaru Y., Okamoto K., Ueyama K., Shintani R., and Hyashi T. J. Am. Chem. Soc. 126 (2004) 13584
56. Otomaru Y., Tokunaga N., Shintani R., and Hyashi T. Org. Lett. 7 (2005) 307
57. Wang M.-C., Liu L.-T., Hua L.-T., Hua Y.-Z., Zhang J.-S., Shi Y.-Y., and Wang D.-K. Tetrahedron: Asymmetry 16 (2005) 2531
58. Desrosiers J.-N., Côté A., and Charette A.B. Tetrahedron 61 (2005) 6186
59. Nishimura T., Yasuhara Y., and Hayashi T. Org. Lett. 8 (2006) 979
60. Yamada K.-I., Yamamoto Y., Maekawa M., Akindele T., Umeki H., and Tomioka K. Org. Lett. 8 (2006) 87
61. Friestad G.K., and Mathies A.K. Tetrahedron 63 (2007) 2541
62. Dornow A., Manzel H., and Marx P. Chem. Ber. 97 (1964) 2173
63. Badawy M.A., Abdel-Hady S.A.L., Eid M.M., and Ibrahim Y.A. Chem. Ber. 117 (1984) 1083
64. Mansour A.K., Ibrahim Y.A., and Eid M.M. Z. Naturforsch. 316 (1976) 505
65. Zaher H.A., Mohammedy R., and Ibrahim Y.A. J. Heterocycl. Chem. 21 (1984) 905
66. Konno S., Sagi M., Yashida N., and Yamanaka H. Heterocycles 26 (1987) 3111
67. El-Shehawy A.A. Heteroat. Chem. 14 (2003) 280
68. El-Shehawy A.A. React. Funct. Polym. 55 (2003) 239
69. El-Shehawy A.A. Tetrahedron: Asymmetry 17 (2006) 2617
70. Ramage R., Hopton D., Parrott M.J., Kenner G.W., and Moore G.A. J. Chem. Soc., Perkin Trans. 1 (1984) 1357
71. Pridgen L.N., Mokhallalati M.K., and Wu M.-J. J. Org. Chem. 57 (1992) 1237
72. Yang T.-K., Chen R.-Y., Lee D.-S., Peng W.-S., Jiang Y.-Z., Mi A.-Q., and Jong T.-T. J. Org. Chem. 59 (1994) 914
73. Anderson P.G., Guijarro D., and Tanner D. J. Org. Chem. 62 (1997) 7364
74. Boezio A.A., Pytkowicz J., Côté A., and Charette A.B. J. Am. Chem. Soc. 125 (2003) 14260
75. Hou X.L., Zheng X.L., and Dai L.X. Tetrahedron Lett. 39 (1998) 6949
76. Jimeno C., Vidal-Ferran A., Moyano A., Pericàs M.A., and Riera A. Tetrahedron Lett. 40 (1999) 777
77. Jimeno C., Reddy K.S., Solà L., Moyano A., Pericàs M.A., and Riera A. Org. Lett. 2 (2000) 3157
78. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 984
79. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 10409
80. Sato I., Hosoi K., Kodaka R., and Soai K. Eur. J. Org. Chem. (2002) 3115
81. Itsuno S., El-Shehawy A.A., and Sarhan A.A. React. Polym. 37 (1998) 283
82. Suzuki T., Narisada N., Shibata T., and Soai K. Tetrahedron: Asymmetry 7 (1996) 2519
83. Suzuki T., Narisada N., Shibata T., and Soai K. Polym. Adv. Technol. 10 (1999) 30
84. Soai K., Suzuki T., and Shono T. J. Chem. Soc., Chem. Commun. (1994) 317
85. Suzuki T., Shibata T., and Soai K. J. Chem. Soc., Perkin Trans. 1 (1997) 2757
86. Anderson P.G., Guijarro D., and Tanner D. Synlett (1996) 727
87. Guijarro D., Pinho P., and Anderson P.G. J. Org. Chem. 63 (1998) 2530
88. Brandt P., Hedberg C., Lawonn K., Pinho P., and Anderson P.G. Chem.-Eur. J. 5 (1999) 1692
89. Zhang X.-M., Zhang H.-L., Lin W.Q., Gong L.-Z., Mi A.-Q., Cui X., Jiang Y.-Z., and Yu K. J. Org. Chem. 68 (2003) 4322
90. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley and Sons, New York, NY p 255
91. Yamakawa M., and Noyori R. J. Am. Chem. Soc. 117 (1995) 6327
92. Soai K., Hirose Y., and Ohno Y. Tetrahedron: Asymmetry 4 (1993) 1473
93. Soai K., and Shibata T. J. Synth. Org. Chem. Jpn. 55 (1997) 994
94. Sudbrake C., and Vahrenkamp H. Eur. J. Inorg. Chem. (2001) 751
95. Shu M., Walz R., Wu B., Seebacher J., and Vahrenkamp H. Eur. J. Inorg. Chem. (2003) 2505
96. Suzuki T., Hirokawa Y., Ohtake K., Shibata T., and Soai K. Tetrahedron: Asymmetry 8 (1997) 4033
97. Soai K., Yokoyama S., and Hayasaka T. J. Org. Chem. 56 (1991) 4264