SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 7, 2008, Pages 1076-1080

Formal [2+3] cycloaddition between substituted phenols and allylsilane

(4) Bérard, Didier a Racicot, Léanne a Sabot, Cyrille a Canesi, Sylvain a

a UNIVERSITÉ DU QUÉBEC À MONTRÉAL (Canada)

Author keywords

2+3 cycloaddition; Allyltrimethylsilane; Hypervalent iodine; Substituted phenols

Indexed keywords

ACETOACETIC ACID; ALLYLTRIMETHYLSILANE; IODOBENZENE; PERFLUORO COMPOUND; PHENOL DERIVATIVE;

ARTICLE; CYCLOADDITION; OXIDATION;

EID: 42949088133 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042924 Document Type: Article

Times cited : (42)

References (61)

1
- 0025368319
- (a) Pfefferle, W.; Anke, H.; Bross, M.; Steffan, B. J. Antibiot. 1990, 43, 648.
- (1990) J. Antibiot , vol.43 , pp. 648
- Pfefferle, W.¹ Anke, H.² Bross, M.³ Steffan, B.⁴

2
- 0025252179
- (b) Ayer, W. A.; Nozawa, K. Can. J. Micro. 1990, 36, 83.
- (1990) Can. J. Micro , vol.36 , pp. 83
- Ayer, W.A.¹ Nozawa, K.²

3
- 0000354211
- (a) Allan, R. D.; Correll, R. L.; Wells, R. J. Tetrahedron Lett. 1969, 10, 4673.
- (1969) Tetrahedron Lett , vol.10 , pp. 4673
- Allan, R.D.¹ Correll, R.L.² Wells, R.J.³

4
- 0042531922
- (b) Yamaguchi, S.; Muro, S.; Kobayashi, M.; Miyazawa, M.; Hirai, Y. J. Org. Chem. 2003, 68, 6274.
- (2003) J. Org. Chem , vol.68 , pp. 6274
- Yamaguchi, S.¹ Muro, S.² Kobayashi, M.³ Miyazawa, M.⁴ Hirai, Y.⁵

5
- 0002425120
- (a) Bohlmann, F.; Jakupovic, J.; Schuster, A.; King, R.; Robinson, H. Phytochemistry 1982, 21, 161.
- (1982) Phytochemistry , vol.21 , pp. 161
- Bohlmann, F.¹ Jakupovic, J.² Schuster, A.³ King, R.⁴ Robinson, H.⁵

6
- 0343941770
- (b) Bittner, M.; Jakupovic, J.; Bohlmann, F.; Silva, M. Phytochemistry 1989, 28, 2867.
- (1989) Phytochemistry , vol.28 , pp. 2867
- Bittner, M.¹ Jakupovic, J.² Bohlmann, F.³ Silva, M.⁴

7
- 0000929007
- (c) Asakawa, Y.; Hashimoto, T.; Takikawa, K.; Tori, M.; Ogawa, S. Phytochemistry 1991, 30, 235.
- (1991) Phytochemistry , vol.30 , pp. 235
- Asakawa, Y.¹ Hashimoto, T.² Takikawa, K.³ Tori, M.⁴ Ogawa, S.⁵

8
- 0028325297
- (d) Ahmad-Junan, S. A.; Amos, P. C.; Cockerill, G. S.; Levett, P. C.; Whiting, D. A. Biochem. Soc. Trans. 1994, 22, 237.
- (1994) Biochem. Soc. Trans , vol.22 , pp. 237
- Ahmad-Junan, S.A.¹ Amos, P.C.² Cockerill, G.S.³ Levett, P.C.⁴ Whiting, D.A.⁵

9
- 0031904151
- (e) Banskota, A. H.; Tezuka, Y.; Prasain, J. K.; Matsushige, K.; Saiki, I.; Kadota, S. J. Nat. Prod. 1998, 61, 896.
- (1998) J. Nat. Prod , vol.61 , pp. 896
- Banskota, A.H.¹ Tezuka, Y.² Prasain, J.K.³ Matsushige, K.⁴ Saiki, I.⁵ Kadota, S.⁶

10
- 0037051506
- (f) Céspedes, C. L.; Uchoa, A.; Salazar, J. R.; Perich, F.; Pardo, F. J. Agric. Food Chem. 2002, 50, 2283.
- (2002) J. Agric. Food Chem , vol.50 , pp. 2283
- Céspedes, C.L.¹ Uchoa, A.² Salazar, J.R.³ Perich, F.⁴ Pardo, F.⁵

11
- 0025338714
- (a) Callinan, A.; Chen, Y.; Morrow, G. W.; Swenton, J. S. Tetrahedron Lett. 1990, 31, 4551.
- (1990) Tetrahedron Lett , vol.31 , pp. 4551
- Callinan, A.¹ Chen, Y.² Morrow, G.W.³ Swenton, J.S.⁴

12
- 0001223323
- (b) Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135.
- (1992) J. Org. Chem , vol.57 , pp. 2135
- Gates, B.D.¹ Dalidowicz, P.² Tebben, A.³ Wang, S.⁴ Swenton, J.S.⁵

13
- 0028028343
- (c) Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529.
- (1994) Tetrahedron Lett , vol.35 , pp. 7529
- Kerns, M.L.¹ Conroy, S.M.² Swenton, J.S.³

14
- 0027946076
- (d) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
- (1994) J. Org. Chem , vol.59 , pp. 6588
- Engler, T.A.¹ Wei, D.² Letavic, M.A.³ Combrink, K.D.⁴ Reddy, J.P.⁵

15
- 0028032445
- (e) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O. Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567.
- (1994) J. Org. Chem , vol.59 , pp. 6567
- Engler, T.A.¹ Combrink, K.D.² Letavic, M.A.³ Lynch Jr., K.O.⁴ Ray, J.E.⁵

16
- 0003447488
- (f) Ward, R. S. Nat. Prod. Rep. 1995, 183.
- (1995) Nat. Prod. Rep , pp. 183
- Ward, R.S.¹

17
- 0030477506
- (g) Engler, T. A.; Chai, W.; La Tessa, K. O. J. Org. Chem. 1996, 61, 9297.
- (1996) J. Org. Chem , vol.61 , pp. 9297
- Engler, T.A.¹ Chai, W.² La Tessa, K.O.³

18
- 0030858681
- (h) Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978.
- (1997) J. Org. Chem , vol.62 , pp. 6978
- Snider, B.B.¹ Han, L.² Xie, C.³

19
- 0032516356
- (i) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291.
- (1998) Tetrahedron Lett , vol.39 , pp. 3291
- Bolzacchini, E.¹ Brunow, G.² Meinardi, S.³ Orlandi, M.⁴ Rindone, B.⁵ Rummakko, P.⁶ Setala, H.⁷

20
- 0035958473
- (j) Benbow, J. W.; Katoch-Rouse, R. J. Org. Chem. 2001, 66, 4965.
- (2001) J. Org. Chem , vol.66 , pp. 4965
- Benbow, J.W.¹ Katoch-Rouse, R.²

21
- 0035958473
- (k) Benbow, J. W.; Katoch-Rouse, R. J. Org. Chem. 2001, 66, 4965.
- (2001) J. Org. Chem , vol.66 , pp. 4965
- Benbow, J.W.¹ Katoch-Rouse, R.²

22
- 34247208678
- (l) Pelly, S. C.; Govender, S.; Fernande, M. A.; Schmalz, H. G.; Koning, C. B. J. Org Chem. 2007, 72, 2857.
- (2007) J. Org Chem , vol.72 , pp. 2857
- Pelly, S.C.¹ Govender, S.² Fernande, M.A.³ Schmalz, H.G.⁴ Koning, C.B.⁵

23
- 0009566636
- (a) Siegel, A.; Antony, F. Monatsh. Chem. 1955, 86, 292.
- (1955) Monatsh. Chem , vol.86 , pp. 292
- Siegel, A.¹ Antony, F.²

24
- 0000565676
- (b) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
- (1987) J. Org. Chem , vol.52 , pp. 3927
- Tamura, Y.¹ Yakura, T.² Haruta, J.³ Kita, Y.⁴

25
- 1642531695
- (c) Pelter, A.; Drake, R. A. Tetrahedron Lett. 1988, 29, 4181.
- (1988) Tetrahedron Lett , vol.29 , pp. 4181
- Pelter, A.¹ Drake, R.A.²

26
- 0001284394
- (d) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 3684
- Kita, Y.¹ Tohma, H.² Hatanaka, K.³ Takada, T.⁴ Fujita, S.⁵ Mitoh, S.⁶ Sakurai, H.⁷ Oka, S.⁸

27
- 34547196258
- (e) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5854.
- (1996) J. Org. Chem , vol.61 , pp. 5854
- Kita, Y.¹ Takada, T.² Gyoten, M.³ Tohma, H.⁴ Zenk, M.H.⁵ Eichhorn, J.⁶

28
- 0002998144
- (f) Kita, Y.; Gyoten, M.; Ohtsubo, M.; Tohma, H.; Takada, T. Chem. Commun. 1996, 1481.
- (1996) Chem. Commun , pp. 1481
- Kita, Y.¹ Gyoten, M.² Ohtsubo, M.³ Tohma, H.⁴ Takada, T.⁵

29
- 0001158731
- (g) Takada, T.; Arisawa, M.; Gyoten, M.; Hamada, R.; Tohma, H.; Kita, Y. J. Org. Chem. 1998, 63, 7698.
- (1998) J. Org. Chem , vol.63 , pp. 7698
- Takada, T.¹ Arisawa, M.² Gyoten, M.³ Hamada, R.⁴ Tohma, H.⁵ Kita, Y.⁶

30
- 0033531471
- (h) Arisawa, M.; Utsumi, S.; Nakajima, M.; Ramesh, N. G.; Tohma, H.; Kita, Y. Chem. Commun. 1999, 469.
- (1999) Chem. Commun , pp. 469
- Arisawa, M.¹ Utsumi, S.² Nakajima, M.³ Ramesh, N.G.⁴ Tohma, H.⁵ Kita, Y.⁶

31
- 0035819291
- (i) Tohma, H.; Morioka, H.; Takizawa, S.; Arisawa, M.; Kita, Y. Tetrahedron 2001, 57, 345.
- (2001) Tetrahedron , vol.57 , pp. 345
- Tohma, H.¹ Morioka, H.² Takizawa, S.³ Arisawa, M.⁴ Kita, Y.⁵

32
- 0037011068
- (j) Hamamoto, H.; Anilkumar, G.; Tohma, H.; Kita, Y. Chem. Eur. J. 2002, 8, 5377.
- (2002) Chem. Eur. J , vol.8 , pp. 5377
- Hamamoto, H.¹ Anilkumar, G.² Tohma, H.³ Kita, Y.⁴

33
- 0032566026
- (a) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M. Tetrahedron Lett. 1998, 39, 4667.
- (1998) Tetrahedron Lett , vol.39 , pp. 4667
- Braun, N.A.¹ Ciufolini, M.A.² Peters, K.³ Peters, E.-M.⁴

34
- 0034647499
- (b) Braun, N. A.; Bray, J.; Ousmer, M.; Peters, K.; Peters, E.-M.; Bouchu, D.; Ciufolini, M. A. J. Org Chem. 2000, 65, 4397.
- (2000) J. Org Chem , vol.65 , pp. 4397
- Braun, N.A.¹ Bray, J.² Ousmer, M.³ Peters, K.⁴ Peters, E.-M.⁵ Bouchu, D.⁶ Ciufolini, M.A.⁷

35
- 0034807908
- (c) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7534.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 7534
- Ousmer, M.¹ Braun, N.A.² Bavoux, C.³ Perrin, M.⁴ Ciufolini, M.A.⁵

36
- 0037100007
- (d) Canesi, S.; Belmont, P.; Bouchu, D.; Rousset, L.; Ciufolini, M. A. Tetrahedron Lett. 2002, 43, 5193.
- (2002) Tetrahedron Lett , vol.43 , pp. 5193
- Canesi, S.¹ Belmont, P.² Bouchu, D.³ Rousset, L.⁴ Ciufolini, M.A.⁵

37
- 4544303068
- (e) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Angew. Chem. Int. Ed. 2004, 43, 4336;
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 4336
- Canesi, S.¹ Bouchu, D.² Ciufolini, M.A.³

38
- 12444280812
- Angew. Chem. 2004, 116, 4436.
- (2004) Angew. Chem , vol.116 , pp. 4436

39
- 34447311920
- (f) Peuchmaur, M.; Wong, Y.-S. J. Org Chem. 2007, 72, 5374.
- (2007) J. Org Chem , vol.72 , pp. 5374
- Peuchmaur, M.¹ Wong, Y.-S.²

40
- 0037159757
- (a) Akai, S.; Kawashita, N.; Morita, N.; Nakamura, Y.; Iio, K.; Kita, Y. Heterocycles 2002, 58, 75.
- (2002) Heterocycles , vol.58 , pp. 75
- Akai, S.¹ Kawashita, N.² Morita, N.³ Nakamura, Y.⁴ Iio, K.⁵ Kita, Y.⁶

41
- 0037562436
- (b) Zawada, P. V.; Banfield, S. C.; Kerr, M. A. Synlett 2003, 971.
- (2003) Synlett , pp. 971
- Zawada, P.V.¹ Banfield, S.C.² Kerr, M.A.³

42
- 0000179169
- Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56, 435.
- (1991) J. Org. Chem , vol.56 , pp. 435
- Kita, Y.¹ Tohma, H.² Kikuchi, K.³ Inagaki, M.⁴ Yakura, T.⁵

43
- 42949117026
- TFE (pKa ca. 12.4, nucleophilicity ca. -2.8); HFIP (pKa ca. 9.3, nucleophilicity ca. -4.2).
- TFE (pKa ca. 12.4, nucleophilicity ca. -2.8); HFIP (pKa ca. 9.3, nucleophilicity ca. -4.2).

44
- 0034671861
- (a) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem. Int. Ed. 2000, 39, 4593.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 4593
- Scheffler, G.¹ Seike, H.² Sorensen, E.J.³

45
- 0001677413
- (b) Drutu, I.; Njardarson, J. T.; Wood, J. L. Org. Lett. 2002, 4, 493.
- (2002) Org. Lett , vol.4 , pp. 493
- Drutu, I.¹ Njardarson, J.T.² Wood, J.L.³

46
- 13444261090
- (c) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Org. Lett. 2005, 7, 175.
- (2005) Org. Lett , vol.7 , pp. 175
- Canesi, S.¹ Bouchu, D.² Ciufolini, M.A.³

47
- 33646493497
- (d) Ciufolini, M. A.; Canesi, S.; Ousmer, M.; Braun, N. A. Tetrahedron 2006, 62, 5318.
- (2006) Tetrahedron , vol.62 , pp. 5318
- Ciufolini, M.A.¹ Canesi, S.² Ousmer, M.³ Braun, N.A.⁴

48
- 34547218893
- Jean, A.; Cantat, J.; Bérard, D.; Bouchu, D.; Canesi, S. Org. Lett. 2007, 9, 2553.
- (2007) Org. Lett , vol.9 , pp. 2553
- Jean, A.¹ Cantat, J.² Bérard, D.³ Bouchu, D.⁴ Canesi, S.⁵

49
- 35348829739
- Bérard, D.; Jean, A.; Canesi, S. Tetrahedron Lett. 2007, 48, 8238.
- (2007) Tetrahedron Lett , vol.48 , pp. 8238
- Bérard, D.¹ Jean, A.² Canesi, S.³

50
- 0025853780
- (a) Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979.
- (1991) J. Org. Chem , vol.56 , pp. 1979
- Wang, S.¹ Gates, B.D.² Swenton, J.S.³

51
- 0040271482
- (b) Juhasz, L.; Kuerti, L.; Antus, S. J. Nat. Prod. 2000, 63, 866.
- (2000) J. Nat. Prod , vol.63 , pp. 866
- Juhasz, L.¹ Kuerti, L.² Antus, S.³

52
- 0000526337
- Quideau, S.; Looney, M. A.; Pouységu, L. Org. Lett. 1999, 1, 1651.
- (1999) Org. Lett , vol.1 , pp. 1651
- Quideau, S.¹ Looney, M.A.² Pouységu, L.³

53
- 0032509253
- (a) Quideau, S.; Pouységu, L.; Looney, M. A. J. Org. Chem. 1998, 63, 9597.
- (1998) J. Org. Chem , vol.63 , pp. 9597
- Quideau, S.¹ Pouységu, L.² Looney, M.A.³

54
- 0035819303
- (b) Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319.
- (2001) Tetrahedron , vol.57 , pp. 319
- Quideau, S.¹ Pouységu, L.² Oxoby, M.³ Looney, M.A.⁴

55
- 12444256331
- (c) Lebrasseur, N.; Fan, G. J.; Oxoby, M.; Looney, M. A.; Quideau, S. Tetrahedron 2005, 61, 1551.
- (2005) Tetrahedron , vol.61 , pp. 1551
- Lebrasseur, N.¹ Fan, G.J.² Oxoby, M.³ Looney, M.A.⁴ Quideau, S.⁵

56
- 27744511753
- (d) Ozanne-Beaudenon, A.; Quideau, S. Angew. Chem. Int. Ed. 2005, 44, 7065.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 7065
- Ozanne-Beaudenon, A.¹ Quideau, S.²

57
- 36849018131
- (e) Nicolaou, K. C.; Edmonds, D. J.; Li, A.; Tria, G. S. Angew. Chem. Int. Ed. 2007, 119, 4016.
- (2007) Angew. Chem. Int. Ed , vol.119 , pp. 4016
- Nicolaou, K.C.¹ Edmonds, D.J.² Li, A.³ Tria, G.S.⁴

58
- 42949147103
- Reaction effected with HFIP as solvent is easier to purify by chromatography than with TFE as solvent
- Reaction effected with HFIP as solvent is easier to purify by chromatography than with TFE as solvent.

59
- 42949149801
- NMR Data (Table 1) Entry 1: 1H NMR (300 MHz, CDCl3, δ, 7.31 (d, 1 H, J, 1.7 Hz, 7.27 (dd, 1 H, J, 8.2, 1.7 Hz, 6.76 (d, 1 H, J, 8.2 Hz, 4.92 (m, 1 H, 3.29 (dd, 1 H, J, 15.4, 8.2 Hz, 2.81 (dd, 1 H, J, 15.4, 8.2 Hz, 1.34 (dd, 1 H, J, 14.3, 6.6 Hz, 1.11 (dd, 1 H, J, 14.3, 8.8 Hz, 0.24 (s, 9 H, 0.11 (s, 9 H, 13C NMR (75 MHz, CDCl 3, δ, 156.8, 130.8, 128.7, 128.6, 126.4, 122.5, 122.5, 118.5, 112.1, 82.9, 36.9, 25.6, 0.7. Entry 2: 1H NMR (300 MHz, CDCl3, δ= 7.32 (d, 1 H, J, 1.7 Hz, 7.08 (dd, 1 H, J, 8.2, 1.7 Hz, 6.66 (d, 1 H, J, 8.2 Hz, 4.90 (m, 1 H, 3.26 (dd, 1 H, J, 15.4, 8.2 Hz, 2.82 (dd, 1 H, J, 15.4, 8.2 Hz, 1.26 (m, s, 4 H, 1.05 (dd, 1 H, J, 14.3, 8.8 Hz, 0.09 (s, 9 H, 13C NMR 75 MHz, CDCl3, δ, 158.0, 129.4, 127.6, 124.8, 11
- 3): δ = 158.8, 155.7, 149.6, 129.4, 128.7, 122.0, 119.3, 117.3, 117.0, 109.3, 82.7, 38.4, 25.2, -0.8.

60
- 42949157378
- NMR Data Compound 13: 1H NMR (300 MHz, CDCl 3, δ, 7.76 (d, 1 H, J, 8.2 Hz, 7.63 (d, 1 H, J, 8.2 Hz, 7.54 (d, 1 H, J, 8.2 Hz, 7.43 (t, 1 H, J, 8.2 Hz, 7.27 (d, 1 H, J, 8.2 Hz, 7.05 (d, 1 H, J, 8.2 Hz, 5.10 (m, 1 H, 3.56 (dd, 1 H, J, 14.8, 8.8 Hz, 3.03 (dd, 1 H, J, 14.8, 8.2 Hz, 1.37 (dd, 1 H, J, 13.7, 6.6 Hz, 1.18 (dd, 1 H, J, 14.3, 8.8 Hz, 0.11 (s, 9 H, 13C NMR (75 MHz, CDCl 3, δ, 156.8, 130.8, 128.9, 128.7, 128.6, 126.4, 122.5, 122.5, 118.5, 112.1, 82.9, 36.9, 25.6, 0.7. Compound 15: 1H NMR (300 MHz, CDCl3, δ, 6.35 (s, 2 H, 4.92 (m, 1 H, 3.84 (s, 3 H, 3.77 (s, 3 H, 3.22 (dd, 1 H, J, 15.4, 8.2 Hz, 2.79 (dd, 1 H, J, 15.4, 8.2 Hz, 1.42 (dd, 1 H, J, 14.3, 6.6 Hz, 1.19 (dd, 1 H, J, 14.3, 8.8 Hz, 0.10 (s, 9 H, 13C NMR 75 MHz, CDCl3
- 3): δ = 154.4, 144.3, 141.9, 128.3, 101.4, 99.1, 82.9, 56.0, 38.9, 30.9, 25.0, -0.9.

61
- 42949089979
- 3): δ = 154.4, 144.3, 141.8, 138.2, 133.5, 129.1, 128.2, 127.8, 101.3, 99.1, 82.6, 55.9, 38.7, 24.3, -2.2, -2.4.
- 3): δ = 154.4, 144.3, 141.8, 138.2, 133.5, 129.1, 128.2, 127.8, 101.3, 99.1, 82.6, 55.9, 38.7, 24.3, -2.2, -2.4.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.