SCOPUS 정보 검색 플랫폼

Volumn , Issue 7, 2008, Pages 1021-1026

TiCl4/tert-butyl hydroperoxide: Chemioselective oxidation of secondary alcohols and suppression of sharpless epoxidation

(3) Shei, Chun Tin a Chien, Hao Lun a Sung, Kuangsen a

a NATIONAL CHENG KUNG UNIVERSITY (Taiwan)

Author keywords

Alcohol; Epoxidation; Selective oxidation

Indexed keywords

ALCOHOL; TERT BUTYL HYDROPEROXIDE; TITANIUM CHLORIDE; TITANIUM DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL REACTION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY;

EID: 42949102687 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1066997 Document Type: Article

Times cited : (5)

References (45)

1
- 0001394785
- (a) Woodard, S. S.; Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 106.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 106
- Woodard, S.S.¹ Finn, M.G.² Sharpless, K.B.³

2
- 1942447859
- (b) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 113
- Finn, M.G.¹ Sharpless, K.B.²

3
- 0001039136
- (c) McKee, B. H.; Kalantar, T. H.; Sharpless, K. B. J. Org. Chem. 1991, 56, 6966.
- (1991) J. Org. Chem , vol.56 , pp. 6966
- McKee, B.H.¹ Kalantar, T.H.² Sharpless, K.B.³

4
- 18844410382
- (d) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 5765
- Gao, Y.¹ Hanson, R.M.² Klunder, J.M.³ Ko, S.Y.⁴ Masamune, H.⁵ Sharpless, K.B.⁶

5
- 0347599718
- (e) Williams, I. D.; Pedersen, S. F.; Sharpless, K. B.; Lippard, S. J. J. Am. Chem. Soc. 1984, 106, 6430.
- (1984) J. Am. Chem. Soc , vol.106 , pp. 6430
- Williams, I.D.¹ Pedersen, S.F.² Sharpless, K.B.³ Lippard, S.J.⁴

6
- 33845557915
- (f) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yasuhiro, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
- (1981) J. Am. Chem. Soc , vol.103 , pp. 6237
- Martin, V.S.¹ Woodard, S.S.² Katsuki, T.³ Yasuhiro, Y.⁴ Ikeda, M.⁵ Sharpless, K.B.⁶

7
- 0012815040
- (g) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
- (1980) J. Am. Chem. Soc , vol.102 , pp. 5974
- Katsuki, T.¹ Sharpless, K.B.²

8
- 27144511474
- (a) Kelly, A. R.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 14668.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 14668
- Kelly, A.R.¹ Lurain, A.E.² Walsh, P.J.³

9
- 0032496193
- (b) Karjalainen, J. K.; Hormi, O. E. O.; Sherrington, D. C. Tetrahedron: Asymmetry 1998, 9, 1563.
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1563
- Karjalainen, J.K.¹ Hormi, O.E.O.² Sherrington, D.C.³

10
- 33748888565
- (c) Honda, T.; Mizutani, H.; Kanai, K. J. Chem. Soc., Perkin Trans. 1 1996, 1729.
- (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 1729
- Honda, T.¹ Mizutani, H.² Kanai, K.³

11
- 0013130068
- (d) Petersson, H.; Gogoll, A.; Backvall, J.-E. J. Org. Chem. 1992, 57, 6025.
- (1992) J. Org. Chem , vol.57 , pp. 6025
- Petersson, H.¹ Gogoll, A.² Backvall, J.-E.³

12
- 0001280178
- (a) Lu, L. D.-L.; Johnson, R. A.; Finn, M. G.; Sharpless, K. B. J. Org. Chem. 1984, 49, 728.
- (1984) J. Org. Chem , vol.49 , pp. 728
- Lu, L.D.-L.¹ Johnson, R.A.² Finn, M.G.³ Sharpless, K.B.⁴

13
- 0001694607
- (b) Klunder, J. M.; Caron, M.; Uchiyama, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 912.
- (1985) J. Org. Chem , vol.50 , pp. 912
- Klunder, J.M.¹ Caron, M.² Uchiyama, M.³ Sharpless, K.B.⁴

14
- 0003412412
- 5th ed, Wiley-Interscience: New York
- Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; Wiley-Interscience: New York, 2001, 1514-1517.
- (2001) March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure , pp. 1514-1517
- Smith, M.B.¹ March, J.²

15
- 3543000483
- (a) Gogoi, P.; Sarmah, G. K.; Konwar, D. J. Org. Chem. 2004, 69, 5153.
- (2004) J. Org. Chem , vol.69 , pp. 5153
- Gogoi, P.¹ Sarmah, G.K.² Konwar, D.³

16
- 0035802890
- (b) Arterbum, J. B. Tetrahedron 2001, 57, 9765.
- (2001) Tetrahedron , vol.57 , pp. 9765
- Arterbum, J.B.¹

17
- 0000810296
- (c) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041.
- (2001) Org. Lett , vol.3 , pp. 3041
- De Luca, L.¹ Giacomelli, G.² Porcheddu, A.³

18
- 33947202380
- (d) Liu, C.; Han, J.; Wang, J. Synlett 2007, 643.
- (2007) Synlett , pp. 643
- Liu, C.¹ Han, J.² Wang, J.³

19
- 0001472321
- (e) Fung, W.-H.; Yu, W.-Y.; Che, C.-M. J. Org. Chem. 1998, 63, 2873.
- (1998) J. Org. Chem , vol.63 , pp. 2873
- Fung, W.-H.¹ Yu, W.-Y.² Che, C.-M.³

20
- 0029864047
- (f) Krohn, K.; Vinke, I.; Adam, H. J. Org. Chem. 1996, 61, 1467.
- (1996) J. Org. Chem , vol.61 , pp. 1467
- Krohn, K.¹ Vinke, I.² Adam, H.³

21
- 0025182037
- (g) Choudary, B. M.; Durgaprasad, A.; Valli, V. L. K. Tetrahedron Lett. 1990, 31, 5785.
- (1990) Tetrahedron Lett , vol.31 , pp. 5785
- Choudary, B.M.¹ Durgaprasad, A.² Valli, V.L.K.³

22
- 42949138931
- (h) Palombi, L.; Bonadies, F.; Scettri, A.; Mincione, E. Tetrahedron Lett. 1990, 31, 5785.
- (1990) Tetrahedron Lett , vol.31 , pp. 5785
- Palombi, L.¹ Bonadies, F.² Scettri, A.³ Mincione, E.⁴

23
- 84942696548
- (i) Yamawaki, K.; Yoshida, T.; Nishihara, H.; Ishii, Y.; Ogawa, M. Synth. Commun. 1986, 16, 537.
- (1986) Synth. Commun , vol.16 , pp. 537
- Yamawaki, K.¹ Yoshida, T.² Nishihara, H.³ Ishii, Y.⁴ Ogawa, M.⁵

24
- 0000974220
- (j) Masuyama, Y.; Takahashi, M.; Kurusu, Y. Tetrahedron Lett. 1984, 25, 4417.
- (1984) Tetrahedron Lett , vol.25 , pp. 4417
- Masuyama, Y.¹ Takahashi, M.² Kurusu, Y.³

25
- 0000319257
- (k) Kaneda, K.; Kawanishi, Y.; Jitsukawa, K.; Teranishi, S. Tetrahedron Lett. 1983, 24, 5009.
- (1983) Tetrahedron Lett , vol.24 , pp. 5009
- Kaneda, K.¹ Kawanishi, Y.² Jitsukawa, K.³ Teranishi, S.⁴

26
- 33845281994
- (l) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 3786
- Bilgrien, C.¹ Davis, S.² Drago, R.S.³

27
- 0009540446
- (m) Doyle, M. P.; Dow, R. L.; Bagheri, V.; Patrie, W. J. J. Org. Chem. 1983, 48, 476.
- (1983) J. Org. Chem , vol.48 , pp. 476
- Doyle, M.P.¹ Dow, R.L.² Bagheri, V.³ Patrie, W.J.⁴

28
- 33947417725
- (n) Patil, M. L.; Maujan, S. R.; Borate, H. B.; Uphade, B. S. ARKIVOC 2007, (i), 70.
- (2007) ARKIVOC , vol.1 , pp. 70
- Patil, M.L.¹ Maujan, S.R.² Borate, H.B.³ Uphade, B.S.⁴

29
- 33744901725
- (o) Jain, S. L.; Sharma, V. B.; Sain, B. Tetrahedron 2006, 62, 6841.
- (2006) Tetrahedron , vol.62 , pp. 6841
- Jain, S.L.¹ Sharma, V.B.² Sain, B.³

30
- 32244439812
- (p) Boudreau, J.; Doucette, M.; Ajjou, A. N. Tetrahedron 2006, 47, 1695.
- (2006) Tetrahedron , vol.47 , pp. 1695
- Boudreau, J.¹ Doucette, M.² Ajjou, A.N.³

31
- 0344845088
- (q) Ferguson, G.; Ajjou, A. N. Tetrahedron Lett. 2003, 44, 9139.
- (2003) Tetrahedron Lett , vol.44 , pp. 9139
- Ferguson, G.¹ Ajjou, A.N.²

32
- 0000471716
- Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607.
- (1983) J. Org. Chem , vol.48 , pp. 3607
- Hill, J.G.¹ Rossiter, B.E.² Sharpless, K.B.³

33
- 42949111723
- The general procedure for alcohol oxidation with TiCl4/TBHP or Ti(Oi-Pr)4/TBHP is shown as follows. To alcohol substrate 1 (1 mmol) and 4 Å MS (0.5 g) in CHCl3, CH 2Cl2, or CDCl3 (2 mL) at r.t. was added TiCl4 or Ti(Oi-Pr)4 (0.1 mmol, 10% in CHCl 3, The mixture was stirred at r.t. for 1 h. Toluene solution of TBHP (1.7 mmol) was added into the mixture, followed by stirring at r.t. or reflux conditions for 1 or 2 d. Low-boiling-point products 2c and 2d were purified by trap-to-trap fractionation and other products were purified by column chromatography with silica gel as stationary phase and hexane-EtOAc as mobile phase. All the products are known and their characterizations are shown as follows. Compound trans-3a:2d 1H NMR (300 MHz, CDCl3, δ, 3.19 (m, 1 H, 3.78 dd, J, 12.8, 3.5 Hz, 1 H, 3.92
- 3): δ = 25.9, 30.6, 51.5, 63.8, 208.9.

34
- 3042741556
- Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 7277
- Dess, D.B.¹ Martin, J.C.²

35
- 0027771157
- (a) Kawakami, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Org. Chem. 1993, 58, 7608.
- (1993) J. Org. Chem , vol.58 , pp. 7608
- Kawakami, T.¹ Shibata, I.² Baba, A.³ Matsuda, H.⁴

36
- 17444411158
- (b) Murphy, J. A.; Commeureuc, A. G. J.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. Org. Lett. 2005, 7, 1427.
- (2005) Org. Lett , vol.7 , pp. 1427
- Murphy, J.A.¹ Commeureuc, A.G.J.² Snaddon, T.N.³ McGuire, T.M.⁴ Khan, T.A.⁵ Hisler, K.⁶ Dewis, M.L.⁷ Carling, R.⁸

37
- 0000047442
- (c) Amyes, T.; Richard, J. P. J. Am. Chem. Soc. 1992, 114, 10297.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 10297
- Amyes, T.¹ Richard, J.P.²

38
- 0037071234
- (d) Ragagnin, G.; Betzemeier, B.; Quici, S.; Knochel, P. Tetrahedron 2002, 58, 3985.
- (2002) Tetrahedron , vol.58 , pp. 3985
- Ragagnin, G.¹ Betzemeier, B.² Quici, S.³ Knochel, P.⁴

39
- 33846458263
- (e) Fujita, K.-I.; Tanino, N.; Yamaguchi, R. Org. Lett. 2007, 9, 109.
- (2007) Org. Lett , vol.9 , pp. 109
- Fujita, K.-I.¹ Tanino, N.² Yamaguchi, R.³

40
- 0004474274
- (f) Ohwada, T.; Shudo, K. J. Org. Chem. 1989, 54, 5227.
- (1989) J. Org. Chem , vol.54 , pp. 5227
- Ohwada, T.¹ Shudo, K.²

41
- 0006853117
- (g) Okimoto, M.; Itoh, T.; Chiba, T. J. Org. Chem. 1996, 61, 4835.
- (1996) J. Org. Chem , vol.61 , pp. 4835
- Okimoto, M.¹ Itoh, T.² Chiba, T.³

42
- 0001144699
- (h) Tatlock, J. H. J. Org. Chem. 1995, 60, 6221.
- (1995) J. Org. Chem , vol.60 , pp. 6221
- Tatlock, J.H.¹

43
- 0242266536
- (i) Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873.
- (2003) Tetrahedron Lett , vol.44 , pp. 8873
- Chen, J.J.¹ Deshpande, S.V.²

44
- 3543000483
- (j) Gogoi, P.; Sarmah, G. K.; Konwar, D. J. Org. Chem. 2004, 69, 5153.
- (2004) J. Org. Chem , vol.69 , pp. 5153
- Gogoi, P.¹ Sarmah, G.K.² Konwar, D.³

45
- 0001445163
- (k) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S.; Tomasini, C. J. Org. Chem. 1984, 49, 701.
- (1984) J. Org. Chem , vol.49 , pp. 701
- Cardillo, G.¹ Orena, M.² Porzi, G.³ Sandri, S.⁴ Tomasini, C.⁵

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