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77949567603
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For books and reviewes, see
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For books and reviewes, see:
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3
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0003916113
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Padwa A., and Pearson W.H. (Eds), John Wiley and Sons, Hoboken, NJ
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In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products (2003), John Wiley and Sons, Hoboken, NJ
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(2003)
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products
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5
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77949569538
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For representative examples, see
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For representative examples, see
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6
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0034700047
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Hodgson D.M., Bailey J.M., Villalonga-Barber C., Drew M.G.B., and Harrison T. J. Chem. Soc., Perkin Trans. 1 (2000) 3432
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(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 3432
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Hodgson, D.M.1
Bailey, J.M.2
Villalonga-Barber, C.3
Drew, M.G.B.4
Harrison, T.5
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7
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0344875710
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Nakamura S., Hirata Y., Kurosaki T., Anada M., Kataoka O., Kitagaki S., and Hashimoto S. Angew. Chem., Int. Ed. 42 (2003) 5351
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(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5351
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Nakamura, S.1
Hirata, Y.2
Kurosaki, T.3
Anada, M.4
Kataoka, O.5
Kitagaki, S.6
Hashimoto, S.7
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8
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33845447826
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Hirata Y., Nakamura S., Watanabe N., Kataoka O., Kurosaki T., Anada M., Kitagaki S., Shiro M., and Hashimoto S. Chem.-Eur. J. 12 (2006) 8898
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(2006)
Chem.-Eur. J.
, vol.12
, pp. 8898
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Hirata, Y.1
Nakamura, S.2
Watanabe, N.3
Kataoka, O.4
Kurosaki, T.5
Anada, M.6
Kitagaki, S.7
Shiro, M.8
Hashimoto, S.9
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10
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33749856973
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Nakamura S., Sugano Y., Kikuchi F., and Hashimoto S. Angew. Chem., Int. Ed. 45 (2006) 6532
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(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 6532
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Nakamura, S.1
Sugano, Y.2
Kikuchi, F.3
Hashimoto, S.4
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16
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0035887159
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Hodgson D.M., Stupple P.A., Pierard F.Y.T.M., Labande A.H., and Johnstone C. Chem.-Eur. J. 7 (2001) 4465
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(2001)
Chem.-Eur. J.
, vol.7
, pp. 4465
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Hodgson, D.M.1
Stupple, P.A.2
Pierard, F.Y.T.M.3
Labande, A.H.4
Johnstone, C.5
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20
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1842631435
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Hodgson D.M., Brückl T., Glen R., Labande A.H., Selden D.A., Dossetter A.G., and Redgrave A.J. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5450
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(2004)
Proc. Natl. Acad. Sci. U.S.A.
, vol.101
, pp. 5450
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Hodgson, D.M.1
Brückl, T.2
Glen, R.3
Labande, A.H.4
Selden, D.A.5
Dossetter, A.G.6
Redgrave, A.J.7
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22
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0033576992
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Kitagaki S., Anada M., Kataoka O., Matsuno K., Umeda C., Watanabe N., and Hashimoto S. J. Am. Chem. Soc. 121 (1999) 1417
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 1417
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Kitagaki, S.1
Anada, M.2
Kataoka, O.3
Matsuno, K.4
Umeda, C.5
Watanabe, N.6
Hashimoto, S.7
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23
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0034730008
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Kitagaki S., Yasugahira M., Anada M., Nakajima M., and Hashimoto S. Tetrahedron Lett. 41 (2000) 5931
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(2000)
Tetrahedron Lett.
, vol.41
, pp. 5931
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Kitagaki, S.1
Yasugahira, M.2
Anada, M.3
Nakajima, M.4
Hashimoto, S.5
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24
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34547178927
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Tsutsui H., Shimada N., Abe T., Anada M., Nakajima M., Nakamura S., Nambu H., and Hashimoto S. Adv. Synth. Catal. 349 (2007) 521
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(2007)
Adv. Synth. Catal.
, vol.349
, pp. 521
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Tsutsui, H.1
Shimada, N.2
Abe, T.3
Anada, M.4
Nakajima, M.5
Nakamura, S.6
Nambu, H.7
Hashimoto, S.8
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25
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54049087840
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Shimada N., Anada M., Nakamura S., Nambu H., Tsutsuki H., and Hashimoto S. Org. Lett. 10 (2008) 3603
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(2008)
Org. Lett.
, vol.10
, pp. 3603
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Shimada, N.1
Anada, M.2
Nakamura, S.3
Nambu, H.4
Tsutsuki, H.5
Hashimoto, S.6
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26
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65549146503
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Nambu H., Hikime M., Krishnamurthi J., Kamiya M., Shimada N., and Hashimoto S. Tetrahedron Lett. 50 (2009) 3675
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(2009)
Tetrahedron Lett.
, vol.50
, pp. 3675
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Nambu, H.1
Hikime, M.2
Krishnamurthi, J.3
Kamiya, M.4
Shimada, N.5
Hashimoto, S.6
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28
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11844286891
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Suga H., Inoue K., Inoue S., Kakehi A., and Shiro M. J. Org. Chem. 70 (2005) 47
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(2005)
J. Org. Chem.
, vol.70
, pp. 47
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Suga, H.1
Inoue, K.2
Inoue, S.3
Kakehi, A.4
Shiro, M.5
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30
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35548978110
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Suga H., Ishimoto D., Higuchi S., Ohtsuka M., Arikawa T., Tsuchida T., Kakehi A., and Baba T. Org. Lett. 9 (2007) 4359
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(2007)
Org. Lett.
, vol.9
, pp. 4359
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Suga, H.1
Ishimoto, D.2
Higuchi, S.3
Ohtsuka, M.4
Arikawa, T.5
Tsuchida, T.6
Kakehi, A.7
Baba, T.8
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31
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77949569945
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note
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Absolute configuration of the cycloadduct was not determined.
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32
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77949566894
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note
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The endo-adduct is defined as the product in which the more important substituent is on the opposite side of the epoxy bridge, whereas the exo-adduct indicates the product in which the more important substituent is on the same side as the epoxy bridge.
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33
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77949568701
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note
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3: 88% yield, 55% ee.
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34
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77949570226
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note
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3, reflux: 71% yield, 45% ee.
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39
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64549123539
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Suga H., Adachi Y., Fujimoto K., Furihata Y., Tsuchida T., Kakehi A., and Baba T. J. Org. Chem. 74 (2009) 1099
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(2009)
J. Org. Chem.
, vol.74
, pp. 1099
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Suga, H.1
Adachi, Y.2
Fujimoto, K.3
Furihata, Y.4
Tsuchida, T.5
Kakehi, A.6
Baba, T.7
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40
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77949569422
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note
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Although the reason for the switch of the diastereoselectivity in this reaction is not clear at this point, flat structure of the carbonyl ylide for 2-benzopyryrium-4-olates may influence the endo/exo selectivity by inhibition of steric hindrance with vinyl esters. PM3 calculations (heat of formation) of 3f and 28f show that exo-cycloadducts are thermodynamically more stable than endo-cycloadducts, and endo-53a is slightly more stable (0.81 kcal/mol) than the corresponding exo-adduct.
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41
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0035905168
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Desimoni G., Faita G., Filippone S., Mella M., Zampori M.G., and Zema M. Tetrahedron 57 (2001) 10203
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(2001)
Tetrahedron
, vol.57
, pp. 10203
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Desimoni, G.1
Faita, G.2
Filippone, S.3
Mella, M.4
Zampori, M.G.5
Zema, M.6
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49
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0035830555
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Totleben M.J., Prasad J.S., Simpson J.H., Chan S.H., Vanyo D.J., Kuehner D.E., Deshpande R., and Kodersha G.A. J. Org. Chem. 66 (2001) 1057
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(2001)
J. Org. Chem.
, vol.66
, pp. 1057
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Totleben, M.J.1
Prasad, J.S.2
Simpson, J.H.3
Chan, S.H.4
Vanyo, D.J.5
Kuehner, D.E.6
Deshpande, R.7
Kodersha, G.A.8
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50
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0000873253
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Davies I.W., Gerena L., Lu N., Larsen R.D., and Reider P.J. J. Org. Chem. 61 (1996) 9629
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(1996)
J. Org. Chem.
, vol.61
, pp. 9629
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Davies, I.W.1
Gerena, L.2
Lu, N.3
Larsen, R.D.4
Reider, P.J.5
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51
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77949570511
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note
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2-lanthanoid metal complexes, however, the role of the catalyst is probably not only activation of the carbonyl ylide by coordination but also bring the reactants including allyl alcohol close together to achieve the appropriate transition state. The addition of basic inorganic salts may be attributed to the favored coordination of allyl alcohol to the catalyst by hydrogen bonding of allyl alcohol.
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