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For recent reviews on organotrifluoroborates, see: (a) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313-4327.
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Synthesis of a stereotriad having the identical vinyl ends, using the coupling of vinyloxiranes and potassium crotyltrifluoroborates, has been reported. See
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Synthesis of a stereotriad having the identical vinyl ends, using the coupling of vinyloxiranes and potassium crotyltrifluoroborates, has been reported. See: Lautens, M., Ouellet, S. G., Raeppel, S. Angew. Chem., Int. Ed. 2000, 39, 4079-4082.
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0142121846
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Aldehydes 1 were prepared from 2-methyl-1,3-propanediol in two steps. For 1b see: (a) Kiyooka, S.; Shahid, K. A.; Goto, F.; Okazaki, M.; Shuto, Y. J. Org. Chem. 2003, 68, 7967-7978.
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Aldehydes 1 were prepared from 2-methyl-1,3-propanediol in two steps. For 1b see: (a) Kiyooka, S.; Shahid, K. A.; Goto, F.; Okazaki, M.; Shuto, Y. J. Org. Chem. 2003, 68, 7967-7978.
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22
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1842431021
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For 1d see: (b) Kiyooka, S. Tetrahedron: Asymmetry 2003, 14, 2897-2910. 1a and 1c were similarly prepared.
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For 1d see: (b) Kiyooka, S. Tetrahedron: Asymmetry 2003, 14, 2897-2910. 1a and 1c were similarly prepared.
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23
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0025128154
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1H NMR comparisons with the reported data. For 3b-6b and 3d-6d see: (a) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.
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1H NMR comparisons with the reported data. For 3b-6b and 3d-6d see: (a) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.
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24
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34047137043
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1H NMR spectra with 3d-6d and mechanistic considerations.
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1H NMR spectra with 3d-6d and mechanistic considerations.
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25
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85119815222
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7a was prepared from methacrolein and 2,2-dimethyl-1,3-propanediol according to the reported procedure. See: (a) Kelly, T. R.; Fu, Y.; Xie, R. L. Tetrahedron Lett. 1999, 40, 1857-1860.
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7a was prepared from methacrolein and 2,2-dimethyl-1,3-propanediol according to the reported procedure. See: (a) Kelly, T. R.; Fu, Y.; Xie, R. L. Tetrahedron Lett. 1999, 40, 1857-1860.
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26
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4344626586
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For (-)-7b see: (b) Smith, A. B., III; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. Proc. Nat. Acc. Sci. 2004, 101, 12042-12047.
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For (-)-7b see: (b) Smith, A. B., III; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. Proc. Nat. Acc. Sci. 2004, 101, 12042-12047.
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27
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50149087299
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Racemate 7b was prepared from 1d according to the same procedure, (c) For preparation of 7c and 7c′, see the Supporting Information.
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Racemate 7b was prepared from 1d according to the same procedure, (c) For preparation of 7c and 7c′, see the Supporting Information.
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28
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50149089965
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Structure determination of the adducts, see the Supporting Information
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Structure determination of the adducts, see the Supporting Information.
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30
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0007911997
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The β-substituent effects on the aldehyde π-facial selectivity are suggested in the previous reports, see: (a) Hoffmann, R. W, Weidmann, U. Chem. Ber. 1985, 118, 3966-3979
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The β-substituent effects on the aldehyde π-facial selectivity are suggested in the previous reports, see: (a) Hoffmann, R. W.; Weidmann, U. Chem. Ber. 1985, 118, 3966-3979.
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4, MeOH) and the resulting alcohol was identified on the basis of the spectral data reported in the same paper. See the Supporting Information.
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4, MeOH) and the resulting alcohol was identified on the basis of the spectral data reported in the same paper. See the Supporting Information.
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