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Jacobsen E.N., Pfaltz A., Yamamoto H., Eds.; Springer-Verlag Berlin
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Jacobsen, E.N.1
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0001307421
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(a) Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
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Bauld, N.L.1
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79959372443
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The corrected data for the competition experiments have now been reported. See: Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. J. Am. Chem. Soc. 2002, 124, 11223-11223. We have also been unable to reproduce Bauld and Mirafzal radical cation mediated epoxidations described in ref 3.
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Adamo, M.F.A.1
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6
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0037884934
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note
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In the original work this was erroneously reported as 57% ee.
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7
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0031016459
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Bailey, D. J.; O'Hagan, D.; Tavasli, M. Tetrahedron: Asymmetry 1997, 8, 149-153.
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Tavasli, M.3
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8
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0037884939
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note
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(S)-diphenylprolinol 3 was purchased from Aldrich.
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9
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0030576951
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0037070070
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(c) Aggarwal, V. K.; Sandrinelli, F.; Charmant, J. P. H. Tetrahedron: Asymmetry 2002, 13, 87-93.
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0001255039
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(a) Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763-4766.
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(b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236.
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37049101824
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2. The rate of decomposition is maximum at pH 9: Evans, D. F.; Upton, M. W. J. Chem. Soc., Dalton Trans. 1985, 6, 1151-1153.
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3342981841
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For examples of oxidation of amines with Oxone see: Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901-1906.
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0029160418
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(a) For examples of oxidation of amines with Oxone/acetone system see: Brik, M. E. Tetrahedron Lett. 1995, 36, 5519-5522.
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Brik, M.E.1
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Su, Z.; Mariano, P. K.; Falvey, D. E.; Yoon, U. C.; Oh, S. W. J. Am. Chem. Soc. 1998, 120, 10676-10686.
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0001450199
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Murahashi, S.-I.; Imada, Y.; Ohtake, H. J. Org. Chem. 1994, 59, 6170-6172. In the case of 3, the mechanism below could account for the formation of benzophenone and nitrone.
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Murahashi, S.-I.1
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23
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0037547099
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note
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2O.
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26
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37049103954
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(a) For spectroscopic analysis of Oxone, see: Flanagan, J.; Griffith, W. P.; Skapski, A. C. J. Chem. Soc., Chem. Commun. 1984, 1574-1575.
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Flanagan, J.1
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Lester, D.4
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32
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0001349563
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Protonated Oxone (i.e. Oxone at low pH) is a powerful electrophilic oxidant. See: Zhu, W.; Ford, W. T. J. Org. Chem. 1991, 56, 7022-7026.
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Zhu, W.1
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(d) Bowman, R. M.; Collins, J. F.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1972, 626-632.
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39
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0038222506
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note
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2O (Table 3, entry 5).
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40
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0001474702
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There are examples of protonated ammonium salts directing epoxidation through hydrogen bonding with the oxidant (m-CPBA or dimethyloxirane) whilst quaternary ammonium salts gave opposite selectivity. See: (a) Asensio, G.; González-Núñez, M. E.; Boix-Benardini, C.; Mello, R.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250-7253.
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Asensio, G.1
González-Núñez, M.E.2
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Mello, R.4
Adam, W.5
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41
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0033603592
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(b) Asensio. G.; Boix-Benardini, C.; Andreu. C.; González-Núñez, M. E.; Mello, R.; Edwards, J. O.; Carpenter, G. B. J. Org. Chem. 1999, 64, 4705-4711. These reactions are analogous to the seminal work of Henbest27 on hydroxy-directed epoxidations but do not relate to phase transfer catalysed epoxidations of the type described in this paper. Nevertheless, we appreciate one of the reviewers directing us to this work.
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Asensio, G.1
Boix-Benardini, C.2
Andreu, C.3
González-Núñez, M.E.4
Mello, R.5
Edwards, J.O.6
Carpenter, G.B.7
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