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1
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65749095140
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For excellent reviews of NHC-catalyzed reactions, please see
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For excellent reviews of NHC-catalyzed reactions, please see:
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8
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24944439544
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For an example on the effect of reaction conditions in NHC annulations see:
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For an example on the effect of reaction conditions in NHC annulations see:. Sohn S., and Bode J.W. Org. Lett. 7 (2005) 3873-3876
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(2005)
Org. Lett.
, vol.7
, pp. 3873-3876
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Sohn, S.1
Bode, J.W.2
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9
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43549123600
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For an example related to catalyst effects see:
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For an example related to catalyst effects see:. Struble J.R., Kaeobamrung J., and Bode J.W. Org. Lett. 10 (2008) 957-960
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(2008)
Org. Lett.
, vol.10
, pp. 957-960
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Struble, J.R.1
Kaeobamrung, J.2
Bode, J.W.3
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16
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34250822311
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Phillips E.M., Wadamoto M., Chan A., and Scheidt K.A. Angew. Chem., Int. Ed. 46 (2007) 3107-3110
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(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 3107-3110
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Phillips, E.M.1
Wadamoto, M.2
Chan, A.3
Scheidt, K.A.4
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19
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0037455147
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Feling R.H., Buchanan G.O., Mincer T.J., Kauffman C.A., Jensen P.R., and Fenical W. Angew. Chem., Int. Ed. 42 (2003) 355-357
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(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 355-357
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Feling, R.H.1
Buchanan, G.O.2
Mincer, T.J.3
Kauffman, C.A.4
Jensen, P.R.5
Fenical, W.6
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20
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65749102606
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Many total and formal syntheses have been reported: some notable examples are listed here
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Many total and formal syntheses have been reported: some notable examples are listed here:
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23
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34250863260
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Ling T., Macherla V.R., Manam R.R., McArthur K.A., and Potts B.C.M. Org. Lett. 9 (2007) 2289-2292
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(2007)
Org. Lett.
, vol.9
, pp. 2289-2292
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Ling, T.1
Macherla, V.R.2
Manam, R.R.3
McArthur, K.A.4
Potts, B.C.M.5
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25
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55449091166
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Fukuda T., Sugiyama K., Arima S., Harigaya Y., Nagamitsu T., and Ōmura S. Org. Lett. 10 (2008) 4239-4242
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(2008)
Org. Lett.
, vol.10
, pp. 4239-4242
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Fukuda, T.1
Sugiyama, K.2
Arima, S.3
Harigaya, Y.4
Nagamitsu, T.5
Omura, S.6
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29
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65749097201
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note
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First synthesized in our group, we conveniently term 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium chloride as RMesCl. This precatalyst is commercially available from Aldrich, cat. No. 688487.
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30
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33745940097
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For NHC-catalyzed annulations with concomitant decarboxylation of β-lactones see: (a)
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For NHC-catalyzed annulations with concomitant decarboxylation of β-lactones see: (a). Nair V., Vellalath S., Poonoth M., and Suresh E. J. Am. Chem. Soc. 128 (2006) 8736-8737
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(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 8736-8737
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Nair, V.1
Vellalath, S.2
Poonoth, M.3
Suresh, E.4
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32
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65749108259
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See Ref. 6b
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See Ref. 6b.
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35
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0141712450
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Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.-L., Morikawa K., Wang Z.-M., Xu D., and Zhang X.-L. J. Org. Chem. 57 (1992) 2768-2771
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(1992)
J. Org. Chem.
, vol.57
, pp. 2768-2771
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Sharpless, K.B.1
Amberg, W.2
Bennani, Y.L.3
Crispino, G.A.4
Hartung, J.5
Jeong, K.-S.6
Kwong, H.-L.7
Morikawa, K.8
Wang, Z.-M.9
Xu, D.10
Zhang, X.-L.11
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38
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33845282084
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Arduengo III A.J., Stewart C.A., Davidson F., Dixon D.A., Becker J.Y., Culley S.A., and Mizen M.B. J. Am. Chem. Soc. 109 (1987) 627-647
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(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 627-647
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Arduengo III, A.J.1
Stewart, C.A.2
Davidson, F.3
Dixon, D.A.4
Becker, J.Y.5
Culley, S.A.6
Mizen, M.B.7
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39
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33947726600
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Kiviranta P.H., Leppänen J., Rinne V.M., Suuronen T., Kyrylenko O., Kyrylenko S., Kuusisto E., Tervo A.J., Järvinen T., Salminen A., Poso A., and Wallén E.A.A. Bioorg. Med. Chem. Lett. 17 (2007) 2448-2451
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(2007)
Bioorg. Med. Chem. Lett.
, vol.17
, pp. 2448-2451
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Kiviranta, P.H.1
Leppänen, J.2
Rinne, V.M.3
Suuronen, T.4
Kyrylenko, O.5
Kyrylenko, S.6
Kuusisto, E.7
Tervo, A.J.8
Järvinen, T.9
Salminen, A.10
Poso, A.11
Wallén, E.A.A.12
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40
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4744346531
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Davies S.G., Haggitt J.R., Ichihara O., Kelly R.J., Leech M.A., Mortimer A.J.P., Roberts P.M., and Smith A.D. Org. Biomol. Chem. 2 (2004) 2630-2649
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(2004)
Org. Biomol. Chem.
, vol.2
, pp. 2630-2649
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Davies, S.G.1
Haggitt, J.R.2
Ichihara, O.3
Kelly, R.J.4
Leech, M.A.5
Mortimer, A.J.P.6
Roberts, P.M.7
Smith, A.D.8
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41
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65749112166
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note
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1H NMR spectrum for 33 is an exact match to Lam's spectrum, there exists a discrepancy in our reported data at resonance 6.78 ppm due to a typo in Lam's report (δ 6.60 ppm); please see Ref. 8g and Supplementary data therein.
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