IBX/LiBr-promoted one-pot oxidative anti-Markownikov bromohydroxylation/bromoalkoxylation of Baylis-Hillman olefins

Tetrahedron Letters

Volumn 50, Issue 6, 2009, Pages 715-718

  Yadav, Lal Dhar S ^a   Awasthi, Chhama ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

Baylis Hillman adducts; Bromoethers; Bromohydrins; Hypervalent iodine; LiBr; Oxidation

Indexed keywords

2 IODYLBENZOIC ACID; ALKENE DERIVATIVE; BENZOIC ACID DERIVATIVE; LITHIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; HYDROXYLATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 57749182189     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.119     Document Type: Article

References (72)

1. Tenaglia A., Pardigon O., and Buono G. J. Org. Chem. 61 (1996) 1129-1132
2. Haruyoshi M., Kiyoshi T., Masahiro N., Akira H., Yutaka N., and Yasutaka I. J. Org. Chem. 59 (1994) 5550-5555
3. Rodriguez J., and Dulcere J.-P. Synthesis (1993) 1177-1205
4. Block E., and Schwan A.L. In: Trost B.M., Fleming I., and Semmelhack M.F. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon Press, Oxford 344-347
5. Christophersen C. Acta Chem. Scand. 39B (1985) 517-529
6. Erickson R.E. In: Scheuer P.J. (Ed). Marine Natural Products Vol. V (1986), Academic, New York 131
7. Konopelski J.P., Boehler M.A., and Tarasow T.M. J. Org. Chem. 54 (1989) 4966-4970
8. Ullmann's Encyclopedia of Industrial Chemistry, 6th ed.; Electronic Release, 1998.
9. Cabanal-Duvillard I., Berrier J.F., Royer J., and Husson H.P. Tetrahedron Lett. 39 (1998) 5181-5184
10. Ishihara T., Mima K., Konno T., and Yamanaka H. Tetrahedron Lett. 43 (2002) 3493-3497
11. Guindon Y., and Rancourt J. J. Org. Chem. 63 (1998) 6554-6565
12. Nagano H., Kuno Y., Omori Y., and Iguchi M. J. Chem. Soc., Perkin Trans. 1 (1996) 389-394
13. Hart D.J., and Krishnamurthy R. J. Org. Chem. 57 (1992) 4457-4470
14. Smith M.B., and March J. Advanced Organic Chemistry. 5th ed. (2001), Wiley-Interscience, New York p 478
15. Dolenc D., and Harej M. J. Org. Chem. 67 (2002) 312-313
16. Boukhris S., and Souizi A. Tetrahedron Lett. 44 (2003) 3259-3261
17. Boukhris S., Souizi A., and Robert A. Tetrahedron Lett. 39 (1998) 6281-6282
18. Cho S., Kang S., Keum G., Kang S.B., Han S.Y., and Kim Y. J. Org. Chem. 68 (2003) 180-182
19. Adhikari S., and Roy S. Tetrahedron Lett. 33 (1992) 6025-6026
20. Maiti G., Adhikari S., and Roy S.C. J. Chem. Soc., Perkin Trans. 1 (1995) 927-929
21. Maiti G., Adhikari S., and Roy S.C. Tetrahedron 51 (1995) 8389-8396
22. Dulcere J.P., Mihousi M.N., and Rodriguez J. J. Org. Chem. 58 (1993) 5709-5716
23. Singh V., and Batra S. Tetrahedron 64 (2008) 4511-4574
24. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
25. Langer P. Angew. Chem., Int. Ed. 39 (2000) 3049-3052
26. Basavaiah D., and Rao P.D. Tetrahedron 52 (1996) 8001-8062
27. Basavaiah D., Rao V., and Reddy R. J. Chem. Soc. Rev. 36 (2007) 1581-1588
28. Majetich G., Hicks R., and Reister S. J. Org. Chem. 62 (1997) 4321-4326
29. Bonini C., and Righi G. Synthesis (1994) 225-238
30. Smith J.G., and Fieser M. Fieser and Fieser's Reagent for Organic Synthesis Vols. 1-12 (1990), John Wiley and Sons, New York
31. Reddy M.A., Surendra K., Bhanumathi N., and Rama Rao K. Tetrahedron 58 (2002) 6003-6008
32. Sharghi H., Niknam K., and Pooyan M. Tetrahedron 57 (2001) 6057-6064
33. Ranu B.C., and Banerjee S. J. Org. Chem. 70 (2005) 4517-4519
34. Shimizu M., Yoshida A., and Fujisawa T. Synlett (1992) 204-206
35. Ciaccio J.A., Heller E., and Talbot A. Synlett (1991) 248-250
36. Nandanan E., Phukan P., and Sudalai A. Ind. J. Chem. 38B (1999) 283-286
37. In: Larock R.C. (Ed). Comprehensive Organic Transformation: A Guide to Functional Group Preparation. 2nd ed. (1999), Wiley-VCH, New York 629-640
38. Das B., Venkateswarlu K., Damodar K., and Suneel K. J. Mol. Catal. A: Chem. 269 (2007) 17-21
39. Barluenga J., Marco-Arias M., Gonzalez-Bobes F., Ballesteros A., and Gonzalez J.M. Chem. Eur. J. 10 (2004) 1677-1682
40. Masuda H., Takase K., Nishio M., Hasegawa A., Nishiyam Y., and Ishii Y. J. Org. Chem. 59 (1994) 5050-5055
41. Yadav J.S., Reddy B.V.S., Baishya G., and Harshavardhan S.J. Tetrahedron Lett. 46 (2005) 3569-3572
42. Smietna M., Gouverneur V., and Mioskowski C. Tetrahedron Lett. 41 (2000) 193-195
43. Hajra S., Karmakar A., and Bhowmick M. Tetrahedron 61 (2005) 2279-2286
44. Hajra S., Bhowmick M., and Karmakar A. Tetrahedron Lett. 46 (2005) 3073-3077
45. George S., Narina S.V., and Sudalai A. Tetrahedron Lett. 48 (2007) 1375-1378
46. Roy S.C., Guin C., Rana K.K., and Maiti G. Synlett (2001) 226-227
47. Varvoglis A. Hypervalent Iodine in Organic Synthesis (1997), Academic Press, San Diego
48. Wirth T., and Hirt U.H. Synthesis (1999) 1271-1287
49. Stang P.J., and Zhdankin V.V. Chem. Rev. 96 (1996) 1123-1178
50. Kitamura T., and Fujiwara Y. Org. Prep. Proced. Int. 29 (1997) 409-458
51. Wirth T. Angew. Chem., Int. Ed. 40 (2001) 2812-2814
52. Ladziata U., and Zhdankin V.V. Arkivoc ix (2006) 26-58
53. Nicolaou K.C., Montagnon T., and Baran P.S. Angew. Chem., Int. Ed. 41 (2002) 993-996
54. Nicolaou K.C., Barn P.S., Zhong Y.-L., Barluenga S., Hunt K.W., Kranich R., and Vega J.A. J. Am. Chem. Soc. 124 (2002) 2233-2244
55. Yadav J.S., Reddy S., Singh A.P., and Basak A.K. Tetrahedron Lett. 48 (2007) 7546-7548
56. Jang H.S., Chung W.J., and Lee Y.S. Tetrahedron Lett. 48 (2007) 3731-3734
57. Mülbaier M., and Giannis A. Angew. Chem., Int. Ed. 40 (2001) 4393-4394
58. Lei Z., Denecker C., Jegasothy S., Sherrington D.C., Slater N.K.H., and Sutherland A.J. Tetrahedron Lett. 44 (2003) 1635-1637
59. Chung W.J., Kim D.K., and Lee Y.S. Tetrahedron Lett. 44 (2003) 9251-9254
60. Boeckman R.K., Shao P., and Mullins J.J. Org. Synth. Coll. 10 (2004) 696-702
61. Depernet, D.; François, B. U.S. Patent 0107416, 2002; Chem. Abstr. 2002, 137, 109123.
62. Yadav L.D.S., Yadav S., and Rai V.K. Green Chem. 8 (2006) 455-458
63. Yadav L.D.S., and Rai V.K. Tetrahedron Lett. 47 (2006) 395-397
64. Yadav L.D.S., Awasthi C., Rai V.K., and Rai A. Tetrahedron Lett. 48 (2007) 4899-4902 and 8037-8039
65. Yadav L.D.S., Patel R., Rai V.K., and Srivastava V.P. Tetrahedron Lett. 48 (2007) 7793-7795
66. Yadav L.D.S., Rai A., Rai V.K., and Awasthi C. Tetrahedron Lett. 49 (2008) 687-690
67. Yadav L.D.S., Awasthi C., and Rai A. Tetrahedron Lett. 49 (2008) 6360-6363
68. 5: C, 45.57; H, 4.11. Found: C, 45.23; H, 4.43.
69. Rudrawar S. Synlett (2005) 1197-1198
70. 5: C, 60.99; H, 5.08. Found: C, 61.34; H, 5.36.
71. Cai J., Zhou Z., Zhao G., and Tang C. Org. Lett. 4 (2002) 4723-4725
72. 5: C, 48.83; H, 4.94. Found: C, 48.45; H, 4.67.