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1
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0002960755
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Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford
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For review of oxirane chemistry, see: Erden, I. In Comprehensive Heterocyclic Chemistry, 2nd ed.; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1996; Vol. 1A, pp. 97-1369; (b) Sainsbury, M. In Three-, Four-, and Five-membered Monoheterocyclic Compounds. Rodds' Chemistry of Carbon Compounds, 2nd ed.; Second Supplement to Volume IV, Heterocyclic Compounds; Part A, Elsevier: Amsterdam, 1997.
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Erden, I.1
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0012601176
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Rodds' Chemistry of Carbon Compounds, 2nd ed.; Second Supplement to Volume IV, Heterocyclic Compounds; Part A, Elsevier: Amsterdam
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For review of oxirane chemistry, see: Erden, I. In Comprehensive Heterocyclic Chemistry, 2nd ed.; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1996; Vol. 1A, pp. 97-1369; (b) Sainsbury, M. In Three-, Four-, and Five-membered Monoheterocyclic Compounds. Rodds' Chemistry of Carbon Compounds, 2nd ed.; Second Supplement to Volume IV, Heterocyclic Compounds; Part A, Elsevier: Amsterdam, 1997.
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Three-, Four-, and Five-membered Monoheterocyclic Compounds
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Sainsbury, M.1
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For representative examples, see: (a) Lautens, M.; Fagnou, K. Org. Lett. 2000, 2, 2319; (b) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760; (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557; (d) Lin, K.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: London, 2001; Chapter 4, pp. 159-220; (e) Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
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Org. Lett.
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Lautens, M.1
Fagnou, K.2
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4
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0032556198
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For representative examples, see: (a) Lautens, M.; Fagnou, K. Org. Lett. 2000, 2, 2319; (b) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760; (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557; (d) Lin, K.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: London, 2001; Chapter 4, pp. 159-220; (e) Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
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J. Am. Chem. Soc.
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, pp. 10760
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Sodergren, M.J.1
Andersson, P.G.2
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5
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33845378115
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For representative examples, see: (a) Lautens, M.; Fagnou, K. Org. Lett. 2000, 2, 2319; (b) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760; (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557; (d) Lin, K.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: London, 2001; Chapter 4, pp. 159-220; (e) Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
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(1985)
J. Org. Chem.
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, pp. 1557
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Caron, M.1
Sharpless, K.B.2
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6
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0012546050
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Wiley: London; Chapter 4
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For representative examples, see: (a) Lautens, M.; Fagnou, K. Org. Lett. 2000, 2, 2319; (b) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760; (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557; (d) Lin, K.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: London, 2001; Chapter 4, pp. 159-220; (e) Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
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(2001)
Principles and Applications of Asymmetric Synthesis
, pp. 159-220
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Lin, K.-Q.1
Li, Y.-M.2
Chan, A.S.C.3
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7
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33748223147
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For representative examples, see: (a) Lautens, M.; Fagnou, K. Org. Lett. 2000, 2, 2319; (b) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760; (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557; (d) Lin, K.-Q.; Li, Y.-M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley: London, 2001; Chapter 4, pp. 159-220; (e) Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
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(1992)
J. Angew. Chem., Int. Ed. Engl.
, vol.31
, pp. 1179
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Paterson, I.1
Berrisford, D.2
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16
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85031194630
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note
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1,9a,b Many so-called isomerization reactions are actually rearrangement reactions. For instance, the base-catalyzed isomerization of epoxide in Ref. 1a involves the rearrangement of epoxide to allylic alcohol in the presence of a strong base.
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17
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85031198834
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note
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For reviews on acid-mediated rearrangement of epoxides: (a) Rickborn, B. In Comprehensive Organic Synthesis, Carbon-Carbon σ-Bond Formation; Trost, B. M.; Fleming, I., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 3.3, pp. 733-775; (b) Parker, R. E.; Issacs, N. S. Chem. Rev. 1959, 59, 737.
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18
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0035966223
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and references cited therein
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For representative examples of acid-catalyzed rearrangement of epoxides, see: (a) Kita, Y.; Furukawa, A.; Futamura, J.; Ueda, K.; Sawama, Y.; Hamamoto, H.; Fujioka, H. J. Org. Chem. 2001, 66, 8779 and references cited therein; (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379 and references cited therein; (c) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
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J. Org. Chem.
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Kita, Y.1
Furukawa, A.2
Futamura, J.3
Ueda, K.4
Sawama, Y.5
Hamamoto, H.6
Fujioka, H.7
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19
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0029130040
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and references cited therein
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For representative examples of acid-catalyzed rearrangement of epoxides, see: (a) Kita, Y.; Furukawa, A.; Futamura, J.; Ueda, K.; Sawama, Y.; Hamamoto, H.; Fujioka, H. J. Org. Chem. 2001, 66, 8779 and references cited therein; (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379 and references cited therein; (c) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
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J. Am. Chem. Soc.
, vol.117
, pp. 7379
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Jung, M.E.1
D'Amico, D.C.2
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20
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16044372017
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For representative examples of acid-catalyzed rearrangement of epoxides, see: (a) Kita, Y.; Furukawa, A.; Futamura, J.; Ueda, K.; Sawama, Y.; Hamamoto, H.; Fujioka, H. J. Org. Chem. 2001, 66, 8779 and references cited therein; (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379 and references cited therein; (c) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
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J. Org. Chem.
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Hanson, R.M.1
Sharpless, K.B.2
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21
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0001340076
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The mechanism appears to vary for low-valence metal catalysts, see: (a) Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299; (b) Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195; (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611; (d) Suzuki, M.; Dda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623; (e) Eisenmann, J. L. J. Org. Chem. 1962, 27, 2706.
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J. Org. Chem.
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Milstein, D.1
Buchman, O.2
Blum, J.3
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22
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0000756755
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The mechanism appears to vary for low-valence metal catalysts, see: (a) Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299; (b) Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195; (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611; (d) Suzuki, M.; Dda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623; (e) Eisenmann, J. L. J. Org. Chem. 1962, 27, 2706.
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J. Org. Chem.
, vol.59
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Kulawiec, R.J.1
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23
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0000009860
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The mechanism appears to vary for low-valence metal catalysts, see: (a) Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299; (b) Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195; (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611; (d) Suzuki, M.; Dda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623; (e) Eisenmann, J. L. J. Org. Chem. 1962, 27, 2706.
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J. Org. Chem.
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Alper, H.1
Des Roches, D.2
Durst, T.3
Legault, R.4
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24
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0000743544
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The mechanism appears to vary for low-valence metal catalysts, see: (a) Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299; (b) Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195; (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611; (d) Suzuki, M.; Dda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623; (e) Eisenmann, J. L. J. Org. Chem. 1962, 27, 2706.
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J. Am. Chem. Soc.
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Suzuki, M.1
Dda, Y.2
Noyori, R.3
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25
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0001547760
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The mechanism appears to vary for low-valence metal catalysts, see: (a) Milstein, D.; Buchman, O.; Blum, J. J. Org. Chem. 1977, 42, 2299; (b) Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195; (c) Alper, H.; Des Roches, D.; Durst, T.; Legault, R. J. Org. Chem. 1976, 41, 3611; (d) Suzuki, M.; Dda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623; (e) Eisenmann, J. L. J. Org. Chem. 1962, 27, 2706.
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J. Org. Chem.
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Eisenmann, J.L.1
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0001562229
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Gemel C., Trimmel G., Slugovc C., Kremel S., Mereiter K., Schmid R., Kirchner K. Organometallics. 15:1996;3998.
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Organometallics
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Gemel, C.1
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Kremel, S.4
Mereiter, K.5
Schmid, R.6
Kirchner, K.7
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28
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85031208129
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note
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The trans/cis equilibrium ratio of stilbene oxide was found to be 31 upon photolysis at 23°C in pentane. See Ref. 4b.
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29
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85031208431
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note
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5Ru(COD)Cl.
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30
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85031208726
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note
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The cis form of alkynylepoxide 10a has 0.89 kcal/mol less in energy than its trans isomer based on MM2 program (Pro 6.0 edition).
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31
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85031200479
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note
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16 We also prepared authentic (2S,3S)-trans-epoxides 13 and (2S,3R)-cis-epoxide 14, the [α] values of which are used to identify absolute configurations of products isomerized from (2S,3R)-trans-epoxides 13 and (2S,3S)-cis-epoxide 14. For the details, see Supporting information.
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33
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85031199894
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note
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For the stereoelectronic effect of the Tp group on coordination and reaction chemistry, see Ref. 10 and Trofimenko, S. In Scorpinoates: Polypyrazolylborate Ligands and Their Coordination Chemistry; Imperial Press, 1999.
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0037067062
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Yeh K.-L., Liu B., Lo C.-Y., Huang H.-L., Liu R.-S. J. Am. Chem. Soc. 124:2002;6510.
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Yeh, K.-L.1
Liu, B.2
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Huang, H.-L.4
Liu, R.-S.5
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Lo C.-Y., Guo H., Lian J.-J., Shen F.-M., Liu R.-S. J. Org. Chem. 67:2002;3930.
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Lo, C.-Y.1
Guo, H.2
Lian, J.-J.3
Shen, F.-M.4
Liu, R.-S.5
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