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1
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0037123222
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E. J. Corey, T. Shibata, T. W. Lee, J. Am. Chem. Soc. 2002, 124, 3808-3809.
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Corey, E.J.1
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Lee, T.W.3
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D. H. Ryu, T. W. Lee, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 9992-9993.
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Ryu, D.H.1
Lee, T.W.2
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a) D. Liu, E. Canales, E. J. Corey, J. Am. Chem. Soc. 2007, 129, 1498-1499;
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Angew. Chem. Int. Ed
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D. H. Ryu, G. Zhou, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 4800-4802.
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Q.-Y. Hu, P. D. Rege, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 5984-5986.
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Hu, Q.-Y.1
Rege, P.D.2
Corey, E.J.3
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10
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6444234868
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Q.-Y. Hu, G. Zhou, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 13708-13713.
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Hu, Q.-Y.1
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D. H. Ryu, G. Zhou, E. J. Corey, Org. Lett. 2005, 7, 1633-1636.
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Ryu, D.H.1
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33646567839
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Y.-Y. Yeung, S. Hong, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 6310-6311.
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Yeung, Y.-Y.1
Hong, S.2
Corey, E.J.3
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15
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84962350747
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We find that SnCl4 is an excellent activator for Corey's oxazaborolidine 1a. Corey recently reported the use of AlBr3 as an activator for 1a.[4a] Control experiments demonstrate that triflimide-activated catalyst 1a·HNTf2 gives the same major enantiomer as does 1a·SnCl4 see the Supporting Information for details
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4 (see the Supporting Information for details).
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17
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0345491105
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a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
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Lee, C.1
Yang, W.2
Parr, R.G.3
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0033731344
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B. J. Lynch, P. L. Fast, M. Harris, D. G. Truhlar, J. Phys. Chem. A 2000, 104, 4811-4815.
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Lynch, B.J.1
Fast, P.L.2
Harris, M.3
Truhlar, D.G.4
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20
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84962440275
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Justification for the choice of the level of theory is given in the Supporting Information. MP2/6-31G(d) single-point energies were also calculated but they gave inferior results compared to the MPW1K results (see the Supporting Information for details).
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Justification for the choice of the level of theory is given in the Supporting Information. MP2/6-31G(d) single-point energies were also calculated but they gave inferior results compared to the MPW1K results (see the Supporting Information for details).
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21
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84946893847
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a) S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117-129;
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Miertus, S.1
Scrocco, E.2
Tomasi, J.3
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23
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84962440270
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Unless stated otherwise, the discussion refers to the PCM results
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Unless stated otherwise, the discussion refers to the PCM results.
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24
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85022815549
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Indeed, it has been shown that the association of an α,β-enal and a cognate oxazaborolidine catalyst is rapidly reversible on the NMR timescale: E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, J. Am. Chem. Soc. 1992, 114, 8290-8292.
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Indeed, it has been shown that the association of an α,β-enal and a cognate oxazaborolidine catalyst is rapidly reversible on the NMR timescale: E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, J. Am. Chem. Soc. 1992, 114, 8290-8292.
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25
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84962363960
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[1]
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[1]
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26
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84962394169
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It turns out that for all systems investigated the most stable TS has both the smallest enthalpy and Gibbs free energy
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It turns out that for all systems investigated the most stable TS has both the smallest enthalpy and Gibbs free energy.
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27
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84962440252
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-1.
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-1.
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29
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84962426557
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Although the boron center may coordinate to the carbonyl oxygen atom lone pair, which is anti to the dienophile C=C; anti complexation is 5 kJ mol-1 less stable than syn complexation
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-1 less stable than syn complexation.
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30
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33746912011
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E. L. Pearson, L. C. H. Kwan, C. I. Turner, G. A. Jones, A. C. Willis, M. N. Paddon-Row, M S. Sherburn, J. Org. Chem. 2006, 71, 6099-6109.
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J. Org. Chem
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, pp. 6099-6109
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Pearson, E.L.1
Kwan, L.C.H.2
Turner, C.I.3
Jones, G.A.4
Willis, A.C.5
Paddon-Row, M.N.6
Sherburn, M.S.7
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31
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2642662490
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a) J. I. Garcia, V. Martínez-Merino, J. A. Mayoral, L. Salvatella, J. Am. Chem. Soc. 1998, 120, 2415-2420;
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J. Am. Chem. Soc
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Garcia, J.I.1
Martínez-Merino, V.2
Mayoral, J.A.3
Salvatella, L.4
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35
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84962457391
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-1): 4 (6.4); 11 (0.3); 12 (8.7).
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-1): 4 (6.4); 11 (0.3); 12 (8.7).
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36
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84962457388
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2Me group.
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2Me group.
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