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18844410382
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(b) Gao, Y.; Hanson, R. M.; Klunder, J. M.: Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
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Gao, Y.1
Hanson, R.M.2
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Ko, S.Y.4
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(a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 389.
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Corey, E.J.1
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4
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0003417469
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Pattenden, G, Ed, Pergamon Press: Oxford, Chapter 3.3
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(b) Rickborn, B. In Comprehensive Organic Synthesis; Carbon-Carbon α-Bond Formation; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3,Chapter 3.3.
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Comprehensive Organic Synthesis; Carbon-Carbon α-Bond Formation
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Rickborn, B.1
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16
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0141631780
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(k) Jung, M. E.; Hoffmann, B.; Rausch, B.; Contreras, J.-M. Org. Lett. 2003, 5, 3159.
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Org. Lett
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Jung, M.E.1
Hoffmann, B.2
Rausch, B.3
Contreras, J.-M.4
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17
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0345255697
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(l) Jung, M. E.; van den Heuvel, A.; Leach, A. G.; Houk, K. N. Org. Lett. 2003. 5, 3375.
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Jung, M.E.1
van den Heuvel, A.2
Leach, A.G.3
Houk, K.N.4
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22
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34948832038
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For an excellent review of semi-pinacol rearrangements, see
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For an excellent review of semi-pinacol rearrangements, see: Snape, T. J. Chem. Sot: Rev. 2007, 36, 1823.
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Chem. Sot: Rev
, vol.36
, pp. 1823
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Snape, T.J.1
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23
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34247264848
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For recent uses of the non-aldol aldol process, see
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(a) For recent uses of the non-aldol aldol process, see: Mitton-Fry, M. J.: Cullen, A. J.; Sammakia. T. Angew. Chem. Int. Ed. 2007, 46, 1066.
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(2007)
Angew. Chem. Int. Ed
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Mitton-Fry, M.J.1
Cullen, A.J.2
Sammakia, T.3
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25
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4043162596
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(c) Dake, G. R.; Fenster, M. D. B.; Fleury, M.; Patrick, B. O. J. Org. Chem. 2004, 69, 5676.
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J. Org. Chem
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Dake, G.R.1
Fenster, M.D.B.2
Fleury, M.3
Patrick, B.O.4
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27
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58149181923
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The alcohol 7b was too hindered to allow formation of the TBS ether, so the TES ether 7a was used instead.
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The alcohol 7b was too hindered to allow formation of the TBS ether, so the TES ether 7a was used instead.
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28
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58149185666
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This byproduct 9 is seen whenever there is a methyl substituent α to the epoxide and the rearrangement is relatively slow.3f
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3f
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29
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0003050412
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trans-3-Hydroxy 2-methylcyclohexanone: Corey, E. J.: Melvin, L. S., Jr.; Haslanger, M. F. Tetrahedron Lett. 1975, 16, 3117.
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(a) trans-3-Hydroxy 2-methylcyclohexanone: Corey, E. J.: Melvin, L. S., Jr.; Haslanger, M. F. Tetrahedron Lett. 1975, 16, 3117.
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30
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0000484771
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trans-3-Hydroxy- and 3-silyloxy-2-butylcyclohexanone: Tanner, D.; Sellen. M.; Baeckvall, J. E. J. Org. Chem. 1989, 54, 3374.
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(b) trans-3-Hydroxy- and 3-silyloxy-2-butylcyclohexanone: Tanner, D.; Sellen. M.; Baeckvall, J. E. J. Org. Chem. 1989, 54, 3374.
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31
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10244240642
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cis-3-Silyloxy-2,6,6-trimethylcyclohexanone: Keränen, M. D.; Kot, K.; Hollmann, C; Eilbracht P. Org. Biomol. Chem. 2004, 2, 3379.
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(c) cis-3-Silyloxy-2,6,6-trimethylcyclohexanone: Keränen, M. D.; Kot, K.; Hollmann, C; Eilbracht P. Org. Biomol. Chem. 2004, 2, 3379.
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32
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58149200116
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The stereochemistry of these compounds were assigned by analogy to the earlier analogues 8 and 11.
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The stereochemistry of these compounds were assigned by analogy to the earlier analogues 8 and 11.
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33
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58149189011
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There was a strong NOE between the proton α to the OTES group and the aldehyde in 17 which was absent from 16.
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There was a strong NOE between the proton α to the OTES group and the aldehyde in 17 which was absent from 16.
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