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For examples of other oxidative kinetic resolutions, see: (a) Sun, W.; Wang, H.; Xia, C.; Li, J.; Zhao, P. Angew. Chem., Int. Ed. 2003, 42, 1042.
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(a) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202.
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Mueller, J.A.1
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14
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0141847443
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note
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At low (-)-sparteine concentrations where deprotonation is both rate determining and enantiodetermining, exogenous (-)-sparteine acts as a chiral Brønsted base. See ref 5b for details.
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16
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0012253713
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(b) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. Org Lett. 2002, 4, 4179.
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17
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0141624122
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note
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Acetate was introduced into the reaction as the counterion on Pd and the resulting kinetic resolution proved to be poor. See ref 5b for details.
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18
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85050296727
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Kinetic resolution
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rel = ln[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)], where C = conversion and ee = enantiomeric excess. See: Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. Top. Stereochem. 1988, 18, 249.
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Top. Stereochem.
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Kagan, H.B.1
Fiaud, J.C.2
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19
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0141735939
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note
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3, 0.25 mmol (1.0 equiv) of the alcohol or meso diol, and 25 mg of freshly activated crushed molecular sieves (3 Å) were combined. The flask was then attached to the bottom of a reflux condenser. A balloon filled with oxygen gas was then attached to the top of the condenser via a three-way joint. The apparatus was then evacuated (water aspirator) and refilled with oxygen from the balloon three times and heated in an oil bath at 65 °C. Aliquots (0.1 mL) of the reaction were then periodically taken via syringe. The aliquot was quenched with 2% TFA/methanol. The sample was analyzed with use of a GC or HPLC equipped with a chiral column.
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20
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0037420342
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For examples of nonenzymatic desymmetrization of meso diols, see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410.
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Trost, B.M.1
Mino, T.2
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21
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0035996941
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(b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631.
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J. Chem. Soc., Perkin Trans. 1
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Hodgson, R.1
Majid, T.2
Nelson, A.3
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23
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0001591183
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(d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309.
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Harada, T.1
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Suzuki, J.4
Oku, A.5
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24
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0035134880
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(e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61.
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Synlett.
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Harada, T.1
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Oku, A.3
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26
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0032576797
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(g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397.
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Oriyama, T.1
Imai, K.2
Hosoya, T.3
Sano, T.4
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27
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0034704269
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(h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141.
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(2000)
Tetrahedron
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Fujioka, H.1
Nagatomi, Y.2
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Kitagawa, H.4
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0030825714
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(i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
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Kinugasa, M.1
Harada, T.2
Oku, A.3
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29
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0141735937
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note
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See Supporting Information for the isolation, characterization, and X-ray structural data.
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