Tris(pentafluorophenyl)borane-catalyzed alkylation of 1,3-dicarbonyl compounds with benzylic alcohols: Access to oxygenated heterocycles

Synthesis

Volumn , Issue 21, 2010, Pages 3715-3723

  Reddy, Chada Raji ^a   Vijaykumar, Jonnalagadda ^a   Grée, René ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

1,3 dicarbonyl compound; alkylation; benzylic alcohol; heterocycle; tris(pentafluorophenyl)borane

Indexed keywords

ALKYLATING AGENTS; BENZYLIC ALCOHOLS; CHROMENES; DICARBONYL COMPOUNDS; FURANOCOUMARINS; GOOD YIELD; HETEROCYCLES; MONOALKYLATED PRODUCTS; OXYGENATED HETEROCYCLES; TRIS(PENTAFLUOROPHENYL) BORANE;

ALKYLATION;

1 (3 METHYL 1 PHENYL 1H BENZO[F]CHROMEN 2 YL)ETHANONE; 1,3 DICARBONYL; 1,3 DIKETONE; 2 (1,3 DIPHENYLPROP 2 YNYL) 3 HYDROXYCYCLOHEX 2 ENONE; 2 [4 (TERT BUTYLDIMETHYLSILYLOXY) 1 (4 METHOXYPHENYL)BUT 2 YNYL] 3 HYDROXY 5,5 DIMETHYLCYCLOHEX 2 ENONE; 2 ALKYL 1,3 DICARBONYL; 2 BENZYL 3 (1 TOSYL 1H INDOL 3 YL) 4H FURO[3,2 C]CHROMEN 4 ONE; 2 BENZYL 3 PHENYL 6,7 DIHYDROBENZOFURAN 4 (5H) ONE; 3 [PHENYL (1 TOSYL 1H INDOL 3 YL)METHYL]PENTANE 2,4 DIONE; 3 ALKYL 4 HYDROXYCOUMARIN DERIVATIVE; 3 HYDROXY 2 [1 (4 METHOXYPHENYL) 4 (TETRAHYDRO 2H PYRAN 2 YLOXY)BUT 2 YNYL] 5,5 DIMETHYLCYCLOHEX 2 ENONE; 3 HYDROXY 2 [5 (4 METHOXYBENZYLOXY) 1 (4 METHOXYPHENYL)PENT 2 YNYL] 5,5 DIMETHYLCYCLOHEX 2 ENONE; 4 ACETYL 2 (4 METHOXYBENZYLIDENE) 5 OXOHEXANITRILE; 4 HYDROXY 3 [3 PHENYL 1 (1 TOSYL 1H INDOL 3 YL)PROP 2 YNYL] 2H CHROMEN 2 ONE; 4 HYDROXY 3 [PHENYL (1 TOSYL 1H INDOL 3 YL)METHYL] 2H CHROMEN 2 ONE; 4 HYDROXYCOUMARIN DERIVATIVE; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; ACETYLACETONE; BENZYL ALCOHOL; BORANE DERIVATIVE; CARBONYL DERIVATIVE; CHROMENE DERIVATIVE; ETHYL 2 BENZHYDRYL 4 CHLORO 3 OXOBUTANOATE; ETHYL 3 OXO 2 [PHENYL (1 TOSYL 1H INDOL 3 YL)METHYL]BUTANOATE; HETEROCYCLIC COMPOUND; TRIS(PENTAFLUOROPHENYL)BORANE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77958565646     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258214     Document Type: Article

References (104)

1. House H O., Modern Synthetic Research 2nd ed. Benjamin Menlopark CA 1972 492
2. Prout F S., Haung E P.-Y, Hartman R J., Korpies C J., J. Am. Chem. Soc. 1954 76 1911
3. Larock R C., Comprehensive Organic Transformations VCH New York 1999
4. Tsuji J, Minami I, Acc. Chem. Res. 1987 20 140
5. Trost B M., Acc. Chem. Res. 1980 13 385
6. Comprehensive Organic Synthesis Vol. 3 Trost B M. Fleming I Pergamon Oxford 1991
7. Marquest J, Moreno-Manas M, Pacheco P, Vallribera A, Tetrahedron Lett. 1988 29 1465
8. Zhu J, You L, Zhao S X., White B, Chen J G., Skonezny P M., Tetrahedron Lett. 2002 43 7585
9. Brandstrom A, Junggren U, Acta Chem. Scand. 1969 23 2204
10. Durst H D., Liebeskind L, J. Org. Chem. 1974 39 3271
11. Ranu B C., Bhar S, J. Chem. Soc., Perkin Trans. 1 1992 365
12. Moreno-Manas M, Marquet J, Vallribera A, Tetrahedron 1996 52 3377
13. Lee H.-S, Park J.-S, Kim B M., Gellmann S H., J. Org. Chem. 2003 68 1575
14. Adams J T., Abramovitch B, Hauser C R., J. Am. Chem. Soc. 1943 65 552
15. Trost B M., Crawley M L., Chem. Rev. 2003 103 2921
16. Ma S, Yu S, Peng Z, Guo H, J. Org. Chem. 2006 71 9865
17. Antonioletti R, Bovicelli P, Malancona S, Tetrahedron 2002 58 589
18. Armugam S, McLeod D, Verkade J G., J. Org. Chem. 1998 63 3677
19. Lei A, Lu X, Org. Lett. 2000 2 2357
20. Konno T, Takehana T, Ishihara T, Yamanaka H, Org. Biomol. Chem. 2004 2 93
21. Dieter R K., Core V K., Chen N, Org. Lett. 2004 6 763
22. Westermaier M, Mayr H, Org. Lett. 2006 8 4791
23. Bandini M, Melloni A, Umani-Ronchi A, Org. Lett. 2004 6 3199
24. DeLaHerran G, Segura A, Csaky A G., Org. Lett. 2007 9 961
25. Muzarat J, Eur. J. Org. Chem. 2007 3077
26. Muzarat J, Tetrahedron 2005 61 4179
27. Tamaru Y, Eur. J. Org. Chem. 2005 2647
28. Kayaki Y, Koda T, Ikaria T, [nl]J. Org. Chem. 2004 69 2595
29. Kinoshita H, Shinokubo H, Oshima K, Org. Lett. 2004 6 4085
30. Manabe K, Kobayashi S, Org. Lett. 2003 5 3241
31. Kimura M, Mukai R, Tanigawa N, Tanaka S, Tamaru Y, Tetrahedron 2003 59 7767
32. Ozawa F, Okamoto H, Kawagishi S, Yamamoto S, Minami T, Yoshifuji M, J. Am. Chem. Soc. 2002 124 10968
33. Mukhopadhyay M, Iqbal J, Tetrahedron Lett. 1995 36 6761
34. Baruah J B., Samuelson A G., J. Organomet. Chem. 1989 361 57
35. 2:, Bisaro F, Prestat G, Vitale M, Poli G, Synlett 2002 1823
36. 3:, Yasuda M, Somyo T, Baba A, Angew. Chem. Int. Ed. 2006 45 1414
37. 3:, Rueping M, Nachtsheim B J., Kuenkel A, Org. Lett. 2007 9 825
38. Metal triflate (Sc, Yb, La, Hf):, Noji M, Kouno Y, Ishii K, J. Org. Chem. 2007 72 5161
39. PTSA:, Sanz T, Miguel D, Martinez A, Alvarez-Gutierrez J M., Rodriguez F, Org. Lett. 2007 9 727
40. 3:, Jana U, Biswas S, Maiti S, Tetrahedron Lett. 2007 48 4065
41. 2:, Rao W, Tay A H. J., Goh P J., Choy J M. L., Ke J K., Chan P W. H., Tetrahedron Lett. 2008 49 122
42. 6:, Kothandaraman P, Rao W, Zhang X X., Chan P W. H., Tetrahedron 2009 65 1833
43. PWA:, Wang G.-W, Shen Y.-B, Wu X.-L, Eur. J. Org. Chem. 2008 4999
44. H-Montmorillonite:, Motokura K, Fujita N, Mori K, Mizugaki T, Ebitani K, Kaneda K, Angew. Chem. Int. Ed. 2006 45 2605
45. TfOH:, Sanz R, Miguel D, Martinez A, Alvarez-Gutierrez J M., Rodriguez F, Org. Lett. 2007 9 2027
46. 2:, Pan Y.-M, Zhao S.-Y, Ji W.-H, Zhan Z.-P, J. Comb. Chem. 2009 11 103
47. EMIOTf:, Funabiki K, Komeda T, Kubota Y, Matsui M, Tetrahedron 2009 65 7457
48. Re catalyst:, Kuninobu Y, Ueda H, Takue K, Chem. Lett. 2008 37 878
49. 2:, Yadav J S., Reddy B V. S., Pandurangam T, Rao K V. R., Praneeth K, Kumar G G. K. S. N., Madhavi C, Kunwar A C., Tetrahedron Lett. 2008 49 4296
50. Formic acid:, Gullickson G C., Lewis D E., Aust. J. Chem. 2003 56 385
51. 3:, Yadav J S., Reddy B V. S., Rao K V. R., Narender R, Tetrahedron Lett. 2009 50 3963
52. Mo(VI) catalyst:, Yang H, Fang L, Zhang M, Zhu C, Eur. J. Org. Chem. 2009 666
53. 2/TMSCl:, Liu C.-R, Li M.-B, Yang C.-F, Tian S.-K, Chem. Eur. J. 2009 15 793
54. 4:, Georgy M, Boucard V, Debleds O, Zotto C D., Campagne J.-M, Tetrahedron 2009 65 1758
55. Transition metal/MW:, Babu S A., Yasuda M, Tsukahara Y, Yamaguchi T, Wada Y, Baba A, Synthesis 2008 1717
56. For alkylation using alcohols in water, see:, Cozzi P G., Zoli L, Angew. Chem. Int. Ed. 2008 47 4162
57. Massey A G., Park A J., Stone F G. A., Proc. Chem. Soc., London 1963 212
58. Massey A G., Park A J., [nl] J. Organomet. Chem. 1964 2 245
59. Massey A G., Park A J., Organometallic Syntheses Vol. 3 King R B. Eisch J J. Elsevier New York 1986 461
60. Marks T J., Acc. Chem. Res. 1992 25 57
61. Yang X, Stern C L., Mark T J., J. Am. Chem. Soc. 1994 116 10015
62. 3, see:, Erker G, Dalton Trans. 2005 1883
63. Kargbo R B., Synlett 2004 1118
64. Ishihara K, Yamamoto H, Eur. J. Org. Chem. 1999 527
65. Chandrasekhar S, Babu B N., Chandrasekhar G, eEROS Encyclopedia Reagents in Organic Synthesis 2006 DOI: 10.1002/047084289X.m00620
66. Rottger D, Schmuck S, Erker G, J. Organomet. Chem. 1996 508 263
67. Bach P, Albright A, Laali K K., Eur. J. Org. Chem. 2009 1961
68. Rubin M, Gevorgyan V, Org. Lett. 2001 3 2705
69. Watson I D. G., Yudin A K., J. Org. Chem. 2003 68 5160
70. Hog D T., Oestreich M, Eur. J. Org. Chem. 2009 5047
71. Gevorgyan V, Liu J.-X, Rubin M, Benson S, Yamamoto Y, Tetrahedron Lett. 1999 40 8919
72. Bajracharya G B., Nogami T, Jin T, Matsuda K, Gevorgyan V, Synthesis 2004 308
73. Chandrasekhar S, Reddy Ch R., Babu B N., Chandrashekar G, Tetrahedron Lett. 2002 43 3801
74. Chandrasekhar S, Reddy Ch R., Babu B N., Chandrashekar G, Tetrahedron Lett. 2004 45 6481
75. Reddy Ch R., Rajesh G, Balaji S V., Chetan N, Tetrahedron Lett. 2008 49 970
76. Reddy Ch R., Jithender E, Tetrahedron Lett. 2009 50 5633
77. Chandrasekhar S, Khatun S, Rajesh G, Reddy Ch R., Tetrahedron Lett. 2009 50 6693
78. Chandrasekhar S, Reddy Ch R., Babu B N., J. Org. Chem. 2002 67 9080
79. Chandrasekhar S, Rao Y S., Mahipal B, Sreelakshimi L, Reddy Ch R., Synthesis 2008 1737
80. Reddy Ch R., Madhavi P P., Reddy A S., Tetrahedron Lett. 2007 48 7169
81. Reddy Ch R., Srikanth B, Rao N N., Shin D.-S, Tetrahedron 2008 64 11666
82. Reddy Ch R., Rao N N., Sudhakar A, Lett. Org. Chem. 2008 5 473
83. Raj G, Kumar R, McKinney W P., Am. J. Med. Sci. 1994 307 128
84. Hadler M R., Shadbolt R S., Nature 1975 253 275
85. Wang S, Milne G W. A., Yan X, Posey I J., Nicklaus M C., Graham L, Rice W G., [nl]J. Med. Chem. 1996 39 2047
86. Enders A, Angew. Chem. 1957 69 481
87. Ziegler R, Monatsh. Chem. 1957 88 25
88. Ahluvalia V K., Arora K K., Mukherjee I, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985 298
89. Huang W, Wang J, Shen Q, Zhou X, Tetrahedron 2007 63 11636
90. Lin X, Dai X, Mao Z, Wang Y, Tetrahedron 2009 65 9233
91. Kischel J, Mertins K, Michalik D, Zapf A, Beller M, Adv. Synth. Catal. 2007 349 865
92. Rueping M, Nachtsheim B J., Sugiono E, Synlett 2010 1549
93. Fan J, Wang Z, Chem. Commun. 2008 5381
94. Ito C, Itoigawa M, Kanematsu T, Ruangrungsi N, Mukainaka T, Tokuda H, Nishino H, Furukawa H, Phytochemistry 2003 64 1265
95. Rukachaisirikul V, Kamkaew M, Sukavisit D, Phongpaichit S, Sawangchote P, Taylor W C., J. Nat. Prod. 2003 66 1531
96. Quaglia W, Pigini M, Piergentili A, Giannella M, Marucci G, Poggesi E, Leonardi A, Melchiorre C, J. Med. Chem. 1999 42 2961
97. Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grandy C, Labreque D, Bubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H, Tseng B, Kasibhatla S, Cai S, J. Med. Chem. 2008 51 417
98. Hardcastle I R., Cockcroft X I., Curtin N J., El-Murr M D., Leahy J J., Stockley M, Golding B T., Regoreau L, Recordson C, Smith G C. M., Grifin J, J. Med. Chem. 2005 48 7829
99. Kidwai M, Saxena S, Khan M K. R., Thukral S S., Bioorg. Med. Chem. Lett. 2005 15 4295
100. For one-pot synthesis of tetrasubstituted furans, see: ref. 6l., Nishibayashi Y, Yoshikawa M, Inada Y, Milton M D., Hidai M, Uemura S, Angew. Chem. Int. Ed. 2003 42 2681
101. Feng X, Tan Z, Chen D, Shen Y, Guo [nl]C.-C, Xiang J, Zhu C, Tetrahedron Lett. 2008 49 4110
102. Ji W.-H, Pan Y.-M, Zhao S.-Y, Zhan Z.-P, Synlett 2008 3046
103. Polivin Y N., Postnov V N., Sazonova V A., Zagorevski D V., Nekrasov Y S., Kharchevnikov A P., [nl]J. Organomet. Chem. 1985 288 201
104. Uozumi Y, Danjo H, Hayashi T, Tetrahedron Lett. 1997 38 3557