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S. S. Woodard, M. G. Finn and K. B. Sharpless, J. Am. Chem. Soc., 1991, 113, 106;
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Woodard, S.S.1
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3
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18844410382
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Y. Gao, J. M. Klunder, R. M. Hanson, H. Masamune, S. Y. Ko and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765;
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Gao, Y.1
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4
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K. B. Sharpless, S. S. Woodard and M. G. Finn, Pure Appl. Chem., 1983, 55, 1823.
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Pure Appl. Chem.
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Sharpless, K.B.1
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5
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0000458209
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For a thorough review on substrate directed transformations see: A. H. Hoveyda, D. A. Evans and G. C. Fu, Chem. Rev., 1993, 93, 1307.
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Chem. Rev.
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Hoveyda, A.H.1
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6
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0037111592
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For selected directed metal catalysed epoxidations see (a) T. J. Donohoe, K. Blades, P. R. Moore, M. J. Waring, J. J. G. Winter, M. Halliwell, N. J. Newcombe and G. Stemp, J. Org. Chem., 2002, 67, 7946;
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Donohoe, T.J.1
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8
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33750598118
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(c) T. Otoh, K. Kaneda and S. Teranishi, J. Chem. Soc., Chem. Commun., 1976, 421;
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Otoh, T.1
Kaneda, K.2
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11
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0016386657
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for selected metal catalysed processes see S. Tanaka, H. Yamamoto, H. Nozaki, K. B. Sharpless, R. C. Michaelson and J. D. Cutting, J. Am. Chem. Soc., 1974, 96, 5254;
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Tanaka, S.1
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Cutting, J.D.6
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15
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0000900117
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The directed syn-epoxidation of mono-N-protected cyclic allylic amides has also been explored with the use of carbamate, amide and sulfonamide N-protecting groups; P. Kocovsky and I. Stary, J. Org. Chem., 1990, 55, 3236;
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Kocovsky, P.1
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0000020774
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L. Goodman, S. Winstein and R. Boschan, J. Am. Chem. Soc., 1958, 80, 4312;
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Goodman, L.1
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37049112534
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J. E. Baldwin, R. M. Adlington, J. Chondrogianni, M. S. Edenborough, J. W. Keeping and C. B. Ziegler, J. Chem. Soc., Chem. Commun., 1985, 816;
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Baldwin, J.E.1
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0001451148
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R. W. Murray, M. Singh, B. L. Williams and H. M. Moncrieff, J. Org. Chem., 1996, 61, 1830;
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Murray, R.W.1
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20
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0001510281
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and ref. 3(a)
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J. E. Bäckvall, K. Oshima, R. E. Palermo and K. B. Sharpless, J. Org. Chem., 1979, 44, 1953 and ref. 3(a).
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J. Org. Chem.
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Bäckvall, J.E.1
Oshima, K.2
Palermo, R.E.3
Sharpless, K.B.4
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21
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0000756880
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For a study using acyclic carbamates see A. Jenmalm, W. Berts, K. Luthman, I. Csöregh and U. Hacksell, J. Org. Chem., 1995, 60, 1026.
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Jenmalm, A.1
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Hacksell, U.5
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22
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0346656525
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O'Brien et al. have reported recently the diastereoselective trans-epoxidation of di-N-protected cyclic allylic amines using combinations of the same protecting groups; P. O'Brien, A. C. Childs, G. J. Ensor, C. L. Hill, J. P. Kirby, M. J. Dearden, S. J. Oxenford and C. M. Rosser, Org. Lett., 2003, 5, 4955.
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Dearden, M.J.6
Oxenford, S.J.7
Rosser, C.M.8
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23
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0040415524
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Sharpless et al. have used the susceptibility of amines to N-oxidation to effect kinetic resolution by enantioselective N-oxide formation; see S. Miyano, L. D.-L. Lu, S. M. Viti and K. B. Sharpless, J. Org. Chem., 1983, 48, 3608;
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J. Org. Chem.
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Miyano, S.1
Lu, L.D.-L.2
Viti, S.M.3
Sharpless, K.B.4
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24
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0001274664
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S. Miyano, L. D.-L. Lu, S. M. Viti and K. B. Sharpless, J. Org. Chem., 1985, 50, 4350.
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J. Org. Chem.
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Miyano, S.1
Lu, L.D.-L.2
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Sharpless, K.B.4
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25
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0000351426
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G. Asensio, R. Mello, C. Boix-Bernardini, M. E. González- Núñez and G. Castellano, J. Org. Chem., 1995, 60, 3692;
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Asensio, G.1
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Castellano, G.5
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26
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0033603592
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G. Asensio, C. Boix-Bernardini, C. Andreu, M. E. González- Núñez, R. Mello, J. O. Edwards and G. Castellano, J. Org. Chem., 1999, 64, 4705.
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Asensio, G.1
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Castellano, G.7
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27
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0001474702
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G. Asensio, M. E. González-Núñez, C. B. Bernardini, R. Mello and W. Adam, J. Am. Chem. Soc., 1993, 115, 7250.
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Asensio, G.1
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Mello, R.4
Adam, W.5
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28
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0043262859
-
-
3 has been reported to protect the N-atom of tertiary alkenylamines from oxidation by dioxiranes; see M. Ferrer, F. Sanchez-Baeza, A. Messeguer, A. Diez and M. Rubiralta, J. Chem. Soc., Chem. Commun., 1995, 293.
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J. Chem. Soc., Chem. Commun.
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Ferrer, M.1
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0036305675
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A. S. Edwards, R. A. J. Wybrow, C. Johnstone, H. Adams and J. P. A. Harrity, Chem. Commun., 2002, 1542.
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Chem. Commun.
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Edwards, A.S.1
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Adams, H.4
Harrity, J.P.A.5
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30
-
-
0041409710
-
-
For related stereoselective oxidations within this laboratory see S. G. Davies, M.-S. Key, H. R. Solla, H. J. Sanganee, E. D. Savory and A. D. Smith, Synlett, 2003, 1659.
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Synlett
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Davies, S.G.1
Key, M.-S.2
Solla, H.R.3
Sanganee, H.J.4
Savory, E.D.5
Smith, A.D.6
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31
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-
0042160897
-
-
For a related topic see L. Gil, D. Compère, B. Guilloteau-Bertin, A. Chiaroni and C. Marazano, Synthesis, 2000, 2117.
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Synthesis
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Gil, L.1
Compère, D.2
Guilloteau-Bertin, B.3
Chiaroni, A.4
Marazano, C.5
-
32
-
-
26444457829
-
-
note
-
max (film) 3412 (O-H) .
-
-
-
-
33
-
-
37049138320
-
-
In this analysis, it is assumed that the pseudoequatorial ammonium ion is more efficient at directing epoxidation than the pseudoaxial conformer; this has been postulated in the analogous directed epoxidation of allylic alcohols with mCPBA; P. Chamberlain, M. L. Roberts and G. H. Whitham, J. Chem. Soc. (B), 1970, 1374.
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(1970)
J. Chem. Soc. (B)
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Chamberlain, P.1
Roberts, M.L.2
Whitham, G.H.3
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34
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0342476400
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S. Winstein, C. Hanson and E. Grunwald, J. Am. Chem. Soc., 1948, 70, 812.
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J. Am. Chem. Soc.
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Winstein, S.1
Hanson, C.2
Grunwald, E.3
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