Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxy-2,6-diethynylbenzene: synthesis and application to diethylzinc addition to aldehydes

Tetrahedron Asymmetry

Volumn 18, Issue 17, 2007, Pages 2016-2020

  Jammi, Suribabu ^a   Rout, Laxmidhar ^a   Punniyamurthy, Tharmalingam ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIALKOXY 2,6 DIETHYNYLBENZENE; ALDEHYDE; BENZENE DERIVATIVE; DIETHYLZINC; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 34748902241     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.004     Document Type: Article

References (60)

1. Muniz-Fernandez K., and Bolm C. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis (1998), Wiley-VCH, Weinheim 271
2. Punniyamurthy T., Velusamy S., and Iqbal J. Chem. Rev. 105 (2005) 2329
3. Jacobsen E.N. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (1993), VCH, Weinheim 159
4. Katsuki T. Chem. Soc. Rev. 33 (2004) 437
5. Jacobsen E.N. Acc. Chem. Res. 33 (2000) 421
6. Bhatia B., Punniyamurthy T., and Iqbal J. In: Katsuki T. (Ed). Asymmetric Oxidation Reactions (2000), Oxford University Press, New York 1
7. Katsuki T. Coord. Chem. Rev. 140 (1995) 189
8. Bennani Y.L., and Hanessian S. Tetrahedron 52 (1996) 13837
9. For some of the recent studies:. Cho S.-H., Ma B., Nguyen S.T., Hupp J.T., and Albrecht-Schmitt T.E. Chem. Commun. (2006) 2563
10. Kim S.S. Pure Appl. Chem. 78 (2006) 977
11. Cozzi P.G. Angew. Chem., Int. Ed. 45 (2006) 2951
12. Balskus E.P., and Jacobsen E.N. J. Am. Chem. Soc. 128 (2006) 6810
13. Kwiatkowski P., Chaladaj W., and Jurczak J. Tetrahedron 62 (2006) 5116
14. Li G.-Y., Zhang J., Chan P.W.H., Xu Z.-J., Zhu N., and Che C.-M. Organometallics 25 (2006) 1676
15. Reeve T.B., Cros J.-P., Gennari C., Piarulli U., and de Vries J.G. Angew. Chem., Int. Ed. 45 (2006) 2449
16. BeIokon Y.N., Ishibashi E., Nomura H., and North M. Chem. Commun. (2006) 1775
17. Cossi P.G., and Kotrusz P. J. Am. Chem. Soc. 128 (2006) 4940
18. Cho Y.-H., Fayol A., and Lautens M. Tetrahedron: Asymmetry 17 (2006) 416
19. Rossbach B.M., Leopaold K., and Weberskirch R. Angew. Chem., Int. Ed. 45 (2006) 1309
20. Bhattacharjee S., and Anderson J.A. Adv. Synth. Catal. 348 (2006) 151
21. Martinez A., Hemmert C., Loup C., Barre G., and Meunier B. J. Org. Chem. 71 (2006) 1449
22. Zhao S., Zhao J., and Zhao D. Carbohydrate Res. 342 (2007) 254
23. Chaldaj W., Kwiatkowski P., Majer J., and Jurczak J. Tetrahedron Lett. 48 (2007) 2405
24. Nakamura Y., Egami H., Matsumoto K., Uchida T., and Katsuki T. Tetrahedron 63 (2007) 6383
25. Jiang J.-J., and Shi M. Tetrahedron: Asymmetry 18 (2007) 1376
26. Berkessel A., and Brandenburg M. Org. Lett. 8 (2006) 4401
27. Lou L.L., Yu K., Ding F., Zhou W., Peng X., and Liu S. Tetrahedron Lett. 47 (2006) 6513
28. Baleizao C., and Garcia H. Chem. Rev. 106 (2006) 3987
29. Holbach M., and Weck M. J. Org. Chem. 71 (2006) 1825
30. Zheng X., Jones C.W., and Weck M. Chem. Eur. J. 12 (2006) 576
31. Ready J.M., and Jacobsen E.N. J. Am. Chem. Soc. 123 (2001) 2687
32. Lere-Porte J.-P., Moreau J.J.E., Serein-Spirau F., and Wakim S. Chem. Commun. (2002) 3020
33. Zheng X., Jones C.W., and Weck M. Chem. Eur. J. 12 (2006) 576
34. Pu L. Chem. Eur. J. 5 (1999) 2227
35. Velusamy S., Ahamed M., and Punniyamurthy T. Org. Lett. 6 (2004) 4821
36. Punniyamurthy, T. Rout, L. Coord. Chem. Rev., in press, doi:10.1016/j.ccr.2007.04.003.
37. Rout L., Nath P., and Punniyamurthy T. Adv. Synth. Catal. 349 (2007) 846
38. Sellner H., Karjalainen J.K., and Seebach D. Chem. Eur. J. 7 (2001) 2873
39. 25 = + 376 (c 0.1, THF). Anal. Calcd: C, 79.76; H, 8.92; N, 3.44. Found: C, 79.20; H, 9.10; N, 3.40.
40. 3). Anal. Calcd: C, 82.09; H, 7.22; N, 3.08. Found: C, 81.88; H, 7.29; N, 3.10.
41. Harada N., and Nakanishi K. Circular Dichroic Spectroscopy (1983), Oxford University Press, Oxford
42. Kawai M., Nagai U., and Katsumi M. Tetrahedron Lett. (1975) 3165
43. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 50 (1975) 4467
44. Weden C., and Wirghton M.S. Macromolecules 29 (1996) 5157
45. 2O. The combined organic layer was concentrated to 1 ml and treated with MeOH to precipitate polymer 1a or 1b. The filtrate was evaporated on a rotary evaporator and the residue passed through a short pad of silica gel (60-120 mesh) using ethyl acetate and hexane (1:19) to afford analytically pure alcohols.
46. For some of recent studies, see:. DiMauro E.F., and Kozlowski M.C. Org. Lett. 3 (2001) 3053
47. Anyanwu U.K., and Venkataraman D. Tetrahedron Lett. 44 (2003) 6445
48. Danilova T.I., Rozenberg V.I., Starikova Z.A., and Brase S. Tetrahedron: Asymmetry 15 (2004) 223
49. Cozzi P.G., Papa A., and Umani-Ronchi A. Tetrahedron Lett. 37 (1996) 4613
50. Vastila P., Pastor I.M., and Adolfsson H. J. Org. Chem. 70 (2005) 2921
51. Hui A., Zhang J., Fan J., and Wang Z. Tetrahedron: Asymmetry 17 (2006) 2101
52. Bauer T., and Gajewiak J. Tetrahedron: Asymmetry 16 (2005) 851
53. Noyori R., and Kitamura M. Angew. Chem., Int. Ed. Engl. 30 (1991) 49
54. Soai K., and Niwa S. Chem. Rev. 92 (1992) 833
55. Pu L., and Yu H.B. Chem. Rev. 101 (2001) 757
56. Ramon D.J., and Yus M. Chem. Rev. 106 (2006) 2126
57. Shi M., and Wang C.-J. Tetrahedron: Asymmetry 13 (2002) 2161
58. Madeda T., Takeuchi T., Furusho Y., and Takata T. J. Polym. Sci. Part A: Polym. Chem. 42 (2004) 4693
59. Pathak K., Bhatt A.P., Abdi S.H.R., Kureshy R.I., Khan N.-U.H., Ahmad I., and Jasra R.V. Chirality 19 (2007) 82
60. Anyanuwu U.K., and Venkataraman D. Tetrahedron Lett. 44 (2003) 6445