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Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg
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(a) Katsuki, T. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 621-648.
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Katsuki, T.1
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2
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Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Heidelberg
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(b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999, 649-677.
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Jacobsen, E.N.1
Wu, M.H.2
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0003544583
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2nd ed, Ojima, I, Ed, Wiley-VCH: New York
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(c) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 231-285.
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Catalytic Asymmetric Synthesis
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Johnson, R.A.1
Sharpless, K.B.2
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4
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0003544583
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2nd ed, Ojima, I, Ed, Wiley-VCH: New York
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(d) Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 287-325.
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Catalytic Asymmetric Synthesis
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Katsuki, T.1
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6
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0037120175
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See, for example: a
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See, for example: (a) Pericàs, M. A.; Puigjaner, C.; Riera, A.; Vidal-Ferran, A.; Gómez, M.; Jimenez, F.; Muller, G.; Rocamora, M. Chem. Eur. J. 2002, 8, 4164.
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(2002)
Chem. Eur. J
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, pp. 4164
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Pericàs, M.A.1
Puigjaner, C.2
Riera, A.3
Vidal-Ferran, A.4
Gómez, M.5
Jimenez, F.6
Muller, G.7
Rocamora, M.8
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7
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35948959734
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and references cited therein
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(b) Popa, D.; Puigjaner, C.; Gómez, M.; Benet-Buchholz, J.; Vidal-Ferran, A.; Pericàs, M. A. Adv. Synth. Catal. 2007, 349, 2265; and references cited therein.
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(2007)
Adv. Synth. Catal
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, pp. 2265
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Popa, D.1
Puigjaner, C.2
Gómez, M.3
Benet-Buchholz, J.4
Vidal-Ferran, A.5
Pericàs, M.A.6
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8
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0034536438
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For leading references on this transformation, see: a
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For leading references on this transformation, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
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(2000)
Synthesis
, pp. 1979
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Frohn, M.1
Shi, Y.2
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10
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1942501759
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(c) Hickey, M.; Goeddel, D.; Crane, Z.; Shi, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5794.
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(2004)
Proc. Natl. Acad. Sci. U.S.A
, vol.101
, pp. 5794
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Hickey, M.1
Goeddel, D.2
Crane, Z.3
Shi, Y.4
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12
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20344404984
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(e) Xia, Q. H.; Ge, H. Q.; Ye, C. P.; Liu, Z. M.; Su, K. X. Chem. Rev. 2005, 105, 1603.
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(2005)
Chem. Rev
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Xia, Q.H.1
Ge, H.Q.2
Ye, C.P.3
Liu, Z.M.4
Su, K.X.5
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13
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0030665236
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and references cited therein
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Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224; and references cited therein.
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(1997)
J. Am. Chem. Soc
, vol.119
, pp. 11224
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Wang, Z.-X.1
Tu, Y.2
Frohn, M.3
Zhang, J.-R.4
Shi, Y.5
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14
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0037205868
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Wu, X. Y.; She, X.; Shi, Y. J. Am. Chem. Soc. 2002, 124, 8792.
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(2002)
J. Am. Chem. Soc
, vol.124
, pp. 8792
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Wu, X.Y.1
She, X.2
Shi, Y.3
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15
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28044472493
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Nieto, N.; Molas, P.; Benet-Buchholz, J.; Vidal-Ferran, A. J. Org. Chem. 2005, 70, 10143.
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(2005)
J. Org. Chem
, vol.70
, pp. 10143
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Nieto, N.1
Molas, P.2
Benet-Buchholz, J.3
Vidal-Ferran, A.4
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16
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56849085860
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Diacetate 2 is a very effective as epoxidation catalyst using 10 mol% of catalyst loading. Loading for Shi's catalysts usually ranges from 20 mol% to 30 mol%. See refs. 4a-c.
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Diacetate 2 is a very effective as epoxidation catalyst using 10 mol% of catalyst loading. Loading for Shi's catalysts usually ranges from 20 mol% to 30 mol%. See refs. 4a-c.
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18
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45449120492
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Nieto, N.; Munslow, I. J.; Barr, J.; Benet-Buchholz, J.; Vidal-Ferran, A. Org. Biomol. Chem. 2008, 6, 2276.
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(2008)
Org. Biomol. Chem
, vol.6
, pp. 2276
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Nieto, N.1
Munslow, I.J.2
Barr, J.3
Benet-Buchholz, J.4
Vidal-Ferran, A.5
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19
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56849126961
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Compound 4e (0.37 g, 46% yield) was obtained as a colourless oil. 1H NMR (400 MHz, CDCl3, δ, 7.27-7.40 (m, 15 H, 6.48 (dt, 1 H, J, 16.0, 1.3 Hz, 6.28 (dt, 1 H, J, 16.0, 6.9 Hz, 5.42 (s, 1 H, 3.62 (t, 2 H, J, 6.9 Hz, 2.60 (qd, 2 H, J, 6.9, 1.3 Hz, 13CNMR: δ, 142.4, 137.7, 131.6, 128.5, 128.4, 127.4, 127.3, 127.2, 127.0, 126.0, 83.7, 68.7, 33.6. The asymmetric epoxidation of alkene 4e to give, )-5e was carried out by the general procedure (see ref. 12, Compound 5e (0.15 g, 52% yield, white solid; mp 56°C; [α]D25 +28.53 (c 0.12, CH 2Cl2, IR: 2871-3066, 1599, 1491, 1097, 1037, 855 cm -1. 1H NMR (400 MHz, CDCl3, δ, 7.12-7.36 (m, 15 H, 5.36 (s, 1 H, 3.69 (d, 1 H, J, 1.9 Hz, 3.65 (t, 2 H, J, 6.0 Hz, 3.13 (td, J, 5.6, 1.9 Hz, 2.02 td, 2 H, J
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R (minor) =11.7 min.
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20
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56849124751
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General Procedure for the Epoxidation of Alkenes: The corresponding alkene (2.22 mmol) and the required amount of catalyst 3 (10-30 mol, were dissolved in MeCN-dimethoxymethane (44 mL, 1:2, A pH 6 buffer solution (8 mL, tetrabutylammonium hydrogen sulfate (35 mg, 0.10 mmol) was slowly added with stirring and the mixture was cooled to the desired temperature. The flask was equipped with two syringe pumps; one of them was filled with a solution of Oxone (3.62-6.82 mmol) in pH 6 buffer (14 mL) and the other one with a solution of K2CO3 (5.33-16.06 mmol) in H2O (14 mL, The two solutions were added dropwise over a 2 h period (syringe pump, The solution was stirred at 0°C for the corresponding reaction time. The mixture was diluted with H2O (40 mL) and extracted with the appropriate organic solvent [5a and 5h: hexane (4 x 40 mL, 5b-g,i-l: CH2Cl2 4 x 40 mL, The combined organic fr
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21 HPLC: Chiralcel AD-H. For 51 GC: gamma dex.
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21
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0028273577
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Higher pH values were not considered since the background reaction could be significant. See
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Higher pH values were not considered since the background reaction could be significant. See: Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577.
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(1994)
Tetrahedron Lett
, vol.35
, pp. 1577
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Kurihara, M.1
Ito, S.2
Tsutsumi, N.3
Miyata, N.4
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22
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0003804449
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1st ed, John Wiley & Sons: Chichester
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Roberts, S. M.; Poignant, G. Catalysis for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction, 1st ed.; John Wiley & Sons: Chichester, 2002, 94-98.
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(2002)
Catalysis for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction
, pp. 94-98
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Roberts, S.M.1
Poignant, G.2
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23
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0030665236
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Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
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(1997)
J. Am. Chem. Soc
, vol.119
, pp. 11224
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Wang, Z.-X.1
Tu, Y.2
Frohn, M.3
Zhang, J.-R.4
Shi, Y.5
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29
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33644531901
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Kin Tse, M.; Bhor, S.; Klawonn, M.; Anilkumar, G.; Jiao, H.; Döbler, C.; Spannenberg, A.; Mägerlein, W.; Hugl, H.; Beller, M. Chem. Eur. J. 2006, 12, 1855.
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(2006)
Chem. Eur. J
, vol.12
, pp. 1855
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Kin Tse, M.1
Bhor, S.2
Klawonn, M.3
Anilkumar, G.4
Jiao, H.5
Döbler, C.6
Spannenberg, A.7
Mägerlein, W.8
Hugl, H.9
Beller, M.10
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