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58149180721
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For recent reviews on gold chemistry, see
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For recent reviews on gold chemistry, see:
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34547510627
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(a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
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(2007)
Chem. Rev
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Hashmi, A.S.K.1
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4
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33845546747
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(c) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896-7936.
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(2006)
Angew. Chem., Int. Ed
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Hashmi, A.S.K.1
Hutchings, G.J.2
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7
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0001718035
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(c) Bagus, P. S.; Lee, Y. S.; Pitzer, K. S. Chem. Phys. Lett. 1975, 33, 408-411.
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(1975)
Chem. Phys. Lett
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Bagus, P.S.1
Lee, Y.S.2
Pitzer, K.S.3
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9
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33845376099
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(a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
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(1986)
J. Am. Chem. Soc
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Ito, Y.1
Sawamura, M.2
Hayashi, T.3
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0032486218
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(b) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1418.
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(1998)
Angew. Chem., Int. Ed
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Teles, J.H.1
Brode, S.2
Chabanas, M.3
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11
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26844516744
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(c) Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 14180-14181.
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(2005)
J. Am. Chem. Soc
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Georgy, M.1
Boucard, V.2
Campagne, J.-M.3
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14
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34247145512
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(f) Lin, C.-C; Teng, T.-M.; Odedra, A.; Liu, R.-S. J. Am. Chem. Soc. 2007, 129, 3798-3799.
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(2007)
J. Am. Chem. Soc
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Lin, C.-C.1
Teng, T.-M.2
Odedra, A.3
Liu, R.-S.4
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17
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36749091693
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Shu, X.-Z.; Liu, X.-Y.; Xiao, H.-Q.; Ji, K.-G.; Guo, L.-N.; Qi, C.-Z.; Liang, Y.-M. Adv. Synth. Catal. 2007, 349, 2493 -2498.
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(2007)
Adv. Synth. Catal
, vol.349
, pp. 2493-2498
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Shu, X.-Z.1
Liu, X.-Y.2
Xiao, H.-Q.3
Ji, K.-G.4
Guo, L.-N.5
Qi, C.-Z.6
Liang, Y.-M.7
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18
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34547935055
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Gold(I)-catalyzed cascade reactions involving cyclization of δ-alkynyl epoxides and further water or alcohol addition were also recently described. See: Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
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Gold(I)-catalyzed cascade reactions involving cyclization of δ-alkynyl epoxides and further water or alcohol addition were also recently described. See: Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
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58149182118
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Hashmi has nevertheless shown that the presence of primary alcohol on the substrate did not affect the formation of furans (Scheme 1, R1, CH2)4OH).5 Therefore, in this case, the nucleophilic alcohol seems to be too far to interact with the alkynyloxirane part
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5 Therefore, in this case, the nucleophilic alcohol seems to be too far to interact with the alkynyloxirane part.
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34249006882
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(a) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752.
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(2007)
Angew. Chem., Int. Ed
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, pp. 2750-2752
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Marion, N.1
Nolan, S.P.2
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33746275648
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(d) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 46, 3647-3650.
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(2006)
Angew. Chem., Int. Ed
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Marion, N.1
Nolan, S.P.2
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17744400103
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(e) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803.
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(2005)
J. Am. Chem. Soc
, vol.127
, pp. 5802-5803
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Shi, X.1
Gorin, D.J.2
Toste, F.D.3
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58149198353
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2/Pd(II) via allene intermediates:
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2/Pd(II) via allene intermediates:
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27
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0035951553
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(a) Aurrecoechea, J. M.; Pérez, E.; Solay, M. J. Org. Chem. 2001, 66, 564-569.
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(2001)
J. Org. Chem
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Aurrecoechea, J.M.1
Pérez, E.2
Solay, M.3
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30
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58149192596
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Ag salts are known to promote rearrangement of propargyl acetoxy derivatives
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Ag salts are known to promote rearrangement of propargyl acetoxy derivatives:
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31
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0014322534
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(a) Benn, W. R. J. Org. Chem. 1968, 33, 3113-3118.
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(1968)
J. Org. Chem
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Benn, W.R.1
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0013074442
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(b) Saimoto, H.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1981, 103, 4975-4977.
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(1981)
J. Am. Chem. Soc
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Saimoto, H.1
Hiyama, T.2
Nozaki, H.3
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33
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0345288250
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(c) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 3078-3087.
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(1983)
Bull. Chem. Soc. Jpn
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Saimoto, H.1
Hiyama, T.2
Nozaki, H.3
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0001215084
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(d) Saimoto, H.; Yukari, K.; Hiyama, T. Tetrahedron Lett. 1986, 27, 1607-1610.
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(1986)
Tetrahedron Lett
, vol.27
, pp. 1607-1610
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Saimoto, H.1
Yukari, K.2
Hiyama, T.3
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0033039614
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(e) Saimoto, H.; Yasui, M.; Ohrai, S-i.; Oikawa, H.; Yokoyama, K.; Shigemasa, Y. Bull. Chem. Soc. Jpn. 1999, 72, 279-284.
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(1999)
Bull. Chem. Soc. Jpn
, vol.72
, pp. 279-284
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Saimoto, H.1
Yasui, M.2
Ohrai, S.-I.3
Oikawa, H.4
Yokoyama, K.5
Shigemasa, Y.6
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36
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0345058933
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(f) Bluthe, N.; Gore, J.; Malacria, M. Tetrahedron 1986, 42, 1333-1344.
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(1986)
Tetrahedron
, vol.42
, pp. 1333-1344
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Bluthe, N.1
Gore, J.2
Malacria, M.3
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37
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58149183032
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1H NMR did not show the presence of intermediates of the Z isomer 2j. However, the faster conversion of one of the two isomers of lj was observed.
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1H NMR did not show the presence of intermediates of the Z isomer 2j. However, the faster conversion of one of the two isomers of lj was observed.
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58149192281
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11) furnished poor yield of divinyl ketone (10 %) but again no trace of furane was observed even after a long contact time.
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11) furnished poor yield of divinyl ketone (10 %) but again no trace of furane was observed even after a long contact time.
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39
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0037186824
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(a) Le Goanvic, D.; Holler, M.; Pale, P. Tetrahedron: Asymmetry 2002, 13, 119-121.
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(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 119-121
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Le Goanvic, D.1
Holler, M.2
Pale, P.3
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0035809375
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(b) Xu, Q.; Wang, G.; Pan, X. Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 381-385.
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(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 381-385
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Xu, Q.1
Wang, G.2
Pan, X.3
Chan, A.S.C.4
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0033862327
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(c) Koning, B.; Buter, J.; Hulst, R.; Stroetinga, R.; Kellogg, R. M. Eur. J. Org. Chem. 2000, 2735-2743.
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(2000)
Eur. J. Org. Chem
, pp. 2735-2743
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Koning, B.1
Buter, J.2
Hulst, R.3
Stroetinga, R.4
Kellogg, R.M.5
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58149192589
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2O gave lk in good yield. See the Supporting Information.
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2O gave lk in good yield. See the Supporting Information.
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0037414928
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(a) Kim, J. T.; Kel'in A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98-101.
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(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 98-101
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Kim, J.T.1
Kel'in, A.V.2
Gevorgyan, V.3
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(b) Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868-9878.
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(2007)
J. Am. Chem. Soc
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Schwier, T.1
Sromek, A.W.2
Yap, D.M.L.3
Chernyak, D.4
Gevorgyan, V.5
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(c) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440-1452.
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J. Am. Chem. Soc
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Dudnik, A.S.1
Sromek, A.W.2
Rubina, M.3
Kim, J.T.4
Kel'in, A.V.5
Gevorgyan, V.6
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58149184466
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Such type of substrates can potentially lead to the formation of the corresponding useful cyclopentenones via the Nazarov reaction. For reviews, see
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Such type of substrates can potentially lead to the formation of the corresponding useful cyclopentenones via the Nazarov reaction. For reviews, see:
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(b) Habermas, K. L.; Denmark, S. E. Org. React. 1994, 45, 1-158, 11971.
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(1994)
Org. React
, vol.45
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Habermas, K.L.1
Denmark, S.E.2
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