-
2
-
-
0026418434
-
-
(b) Trost, B. M. Science 1991, 254, 1471.
-
(1991)
Science
, vol.254
, pp. 1471
-
-
Trost, B.M.1
-
5
-
-
0001353019
-
-
For the synthesis of furans and butenolides see
-
(a) For the synthesis of furans and butenolides see: Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 7255
-
-
Trost, B.M.1
McIntosh, M.C.2
-
6
-
-
0034730992
-
-
For the synthesis of pyrans and related 7-membered oxygen heterocycles see
-
(b) For the synthesis of pyrans and related 7-membered oxygen heterocycles see: Trost, B. M.; Frontier, A. J. J. Am. Chem. Soc. 2000, 122, 11727.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 11727
-
-
Trost, B.M.1
Frontier, A.J.2
-
7
-
-
84889467953
-
-
Lapkin, A., Constable, D. J. C, Eds.; John Wiley & Sons: West Sussex, United Kingdom
-
(a) Andraos, J. In Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes; Lapkin, A., Constable, D. J. C, Eds.; John Wiley & Sons: West Sussex, United Kingdom, 2009, pp 69-200.
-
(2009)
Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes
, pp. 69-200
-
-
Andraos, J.1
-
8
-
-
33750977591
-
-
These and related one-pot reactions have been classified as "cascade reactions." For a recent review on their application in total synthesis see
-
(b) These and related one-pot reactions have been classified as "cascade reactions." For a recent review on their application in total synthesis see: Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 7134
-
-
Nicolaou, K.C.1
Edmonds, D.J.2
Bulger, P.G.3
-
9
-
-
77957981014
-
-
For a general review of pyrrole heterocycle syntheses see:, In, Jones, G., Ramsden, C. A., Eds.; Elsevier: Amsterdam, For reviews regarding the prevalence and biological importance of pyrrole heterocycles see
-
(c) For a general review of pyrrole heterocycle syntheses see: Bergman, J.; Janosik, T. In Comprehensive Heterocyclic Chemistry III; Jones, G., Ramsden, C. A., Eds.; Elsevier: Amsterdam, 2008; Vol. 3, pp 269-351. For reviews regarding the prevalence and biological importance of pyrrole heterocycles see:
-
(2008)
Comprehensive Heterocyclic Chemistry III
, vol.3
, pp. 269-351
-
-
Bergman, J.1
Janosik, T.2
-
10
-
-
45249123879
-
-
(a) Lipkus, A. H.; Yuan, Q.; Lucas, K. A.; Funk, S. A.; Bartelt, W. F.; Schenk, R. J.; Trippe, A. J. J. Org. Chem. 2008, 73, 4443.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 4443
-
-
Lipkus, A.H.1
Yuan, Q.2
Lucas, K.A.3
Funk, S.A.4
Bartelt, W.F.5
Schenk, R.J.6
Trippe, A.J.7
-
11
-
-
38749120651
-
-
(b) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264.
-
(2008)
Chem. Rev.
, vol.108
, pp. 264
-
-
Fan, H.1
Peng, J.2
Hamann, M.T.3
Hu, J.-F.4
-
12
-
-
0031046817
-
-
For the addition of terminal alkynes to electron-poor, internal alkynes see
-
For the addition of terminal alkynes to electron-poor, internal alkynes see: Trost, B. M.; Sorum, M. T.; Chan, C.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 698
-
-
Trost, B.M.1
Sorum, M.T.2
Chan, C.3
Rühter, G.4
-
13
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0035806336
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A reviewer has suggested that coupling of 1 and 2 may involve allene tautomer 1a see below. Our previous success utilizing acceptors 1b and 1d, where competitive formation of 1c was not observed and where formation of an allene intermediate is not possible, respectively, suggests that allene intermediates are not involved. For the use of 1b see reference 2a, and for the use of 1d see
-
A reviewer has suggested that coupling of 1 and 2 may involve allene tautomer 1a (see below). Our previous success utilizing acceptors 1b and 1d, where competitive formation of 1c was not observed and where formation of an allene intermediate is not possible, respectively, suggests that allene intermediates are not involved. For the use of 1b see reference 2a, and for the use of 1d see: Trost, B. M.; Gunzner, J. L.; Yasukata, T. Tetrahedron Lett. 2001, 42, 3775.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 3775
-
-
Trost, B.M.1
Gunzner, J.L.2
Yasukata, T.3
-
14
-
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49649129658
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For a review on the isomerization of alkynoates to enoates see
-
For a review on the isomerization of alkynoates to enoates see: Kwong, C. K.-W.; Fu, M. Y.; Lam, C. S.-L.; Toy, P. H. Synthesis 2008, 2307.
-
(2008)
Synthesis
, pp. 2307
-
-
Kwong, C.K.-W.1
Fu, M.Y.2
Lam, C.S.-L.3
Toy, P.H.4
-
15
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33847309847
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-
For a review of transition-metal-mediated pyrrole syntheses see
-
For a review of transition-metal-mediated pyrrole syntheses see: Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, 121.
-
(2007)
ARKIVOC
, pp. 121
-
-
Patil, N.T.1
Yamamoto, Y.2
-
16
-
-
67549124817
-
-
For related examples see: a
-
For related examples see: (a) Peng, H. M.; Zhao, J.; Li, X. Adv. Synth. Catal. 2009, 351, 1371.
-
(2009)
Adv. Synth. Catal.
, vol.351
, pp. 1371
-
-
Peng, H.M.1
Zhao, J.2
Li, X.3
-
17
-
-
0141431058
-
-
(b) Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 7853
-
-
Gabriele, B.1
Salerno, G.2
Fazio, A.3
-
18
-
-
70350635781
-
-
(c) Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002.
-
(2009)
Org. Lett.
, vol.11
, pp. 5002
-
-
Egi, M.1
Azechi, K.2
Akai, S.3
-
19
-
-
77954637248
-
-
(d) Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 9585
-
-
Rakshit, S.1
Patureau, F.W.2
Glorius, F.3
-
20
-
-
78650613906
-
-
(d) Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326-18339.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 18326-18339
-
-
Stuart, D.R.1
Alsabeh, P.2
Kuhn, M.3
Fagnou, K.4
-
22
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70349769724
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For a recent review of isohypsic reactions in total synthesis see
-
For a recent review of isohypsic reactions in total synthesis see: Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 2854
-
-
Burns, N.Z.1
Baran, P.S.2
Hoffmann, R.W.3
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23
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35549003556
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For a review on the synthesis of substituted pyrroles see
-
For a review on the synthesis of substituted pyrroles see: Schmuck, C.; Rupprecht, D. Synthesis 2007, 3095.
-
(2007)
Synthesis
, pp. 3095
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-
Schmuck, C.1
Rupprecht, D.2
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24
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0032537668
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Isopyrroles related to 4 have been reported:, In addition, isofurans were observed as intermediates in previous work see ref 2a. In both cases, however, the reactivity of these intermediates was not explored
-
Isopyrroles related to 4 have been reported: Larock, R. C.; Doty, M. J.; Han, X. Tetrahedron Lett. 1998, 39, 5143. In addition, isofurans were observed as intermediates in previous work (see ref 2a). In both cases, however, the reactivity of these intermediates was not explored.
-
(1998)
Tetrahedron. Lett.
, vol.39
, pp. 5143
-
-
Larock, R.C.1
Doty, M.J.2
Han, X.3
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25
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36649005330
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Recent efforts in drug discovery have underscored the importance of accessing distinct molecular architectures from a single reaction sequence
-
Recent efforts in drug discovery have underscored the importance of accessing distinct molecular architectures from a single reaction sequence: Gray, B. L.; Schreiber, S. L. J. Comb. Chem. 2007, 9, 1028.
-
(2007)
J. Comb. Chem.
, vol.9
, pp. 1028
-
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Gray, B.L.1
Schreiber, S.L.2
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26
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79851469428
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Acceptor 1 is prepared in two steps from commercially available Boc-propargyl amine. See Supporting Information for details
-
Acceptor 1 is prepared in two steps from commercially available Boc-propargyl amine. See Supporting Information for details.
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-
-
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27
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6444231809
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Wipf, P.; Aoyama, Y.; Benedum, T. E. Org. Lett. 2004, 6, 3593.
-
(2004)
Org. Lett.
, vol.6
, pp. 3593
-
-
Wipf, P.1
Aoyama, Y.2
Benedum, T.E.3
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28
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79851506531
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reaction is tolerant of a variety of solvents. In this study PhMe displayed the best compromise between reaction time and yield
-
The reaction is tolerant of a variety of solvents. In this study PhMe displayed the best compromise between reaction time and yield.
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-
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29
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0003151461
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coordination of TDMPP to Pd has been discussed
-
The coordination of TDMPP to Pd has been discussed: Ma, J.-F.; Kojima, Y.; Yamamoto, Y. J. Organomet. Chem. 2000, 616, 149.
-
(2000)
J. Organomet. Chem.
, vol.616
, pp. 149
-
-
Ma, J.-F.1
Kojima, Y.2
Yamamoto, Y.3
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30
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79851486871
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Attempts to isomerize 3k or 4k to 5k under basic and acidic conditions returned low isolated yields of the desired product. 3k could be cyclized to 5k under thermal conditions but required unacceptably high temperatures >100 °C and reaction times >48 h
-
Attempts to isomerize 3k or 4k to 5k under basic and acidic conditions returned low isolated yields of the desired product. 3k could be cyclized to 5k under thermal conditions but required unacceptably high temperatures (>100 °C) and reaction times (>48 h).
-
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-
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31
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2942566295
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Trofimov, B. A.; Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. I. Chem. Rev. 2004, 104, 2481.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2481
-
-
Trofimov, B.A.1
Sobenina, L.N.2
Demenev, A.P.3
Mikhaleva, A.I.4
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32
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0028600660
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For a related ene reaction using 3-methyleneindolines see
-
For a related ene reaction using 3-methyleneindolines see: Tidwell, J. H.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11797.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 11797
-
-
Tidwell, J.H.1
Buchwald, S.L.2
-
33
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79851490308
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Following complete conversion, the reaction mixture is filtered through a short column of fluorosil to provide analytically pure samples of the isopyrrole. See Supporting Information for details
-
Following complete conversion, the reaction mixture is filtered through a short column of fluorosil to provide analytically pure samples of the isopyrrole. See Supporting Information for details.
-
-
-
-
34
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79851491755
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4 simplified product mixtures which were typically composed of alcohol 6c and the corresponding ketone
-
4 simplified product mixtures which were typically composed of alcohol 6c and the corresponding ketone.
-
-
-
-
35
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79851503366
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Functionalization of 5k would require stoichiometric amounts of activating agents and would reduce the overall atom economy of this process
-
Functionalization of 5k would require stoichiometric amounts of activating agents and would reduce the overall atom economy of this process.
-
-
-
-
36
-
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79851482601
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2 in the conversion of 3k to 5k Table 2. Nevertheless, under the conditions described in Scheme 3, substituted isopyrrole products were not detected. We speculate that the additional additives present under these conditions promote the isomerization of ispoyrrole intermediates into the corresponding pyrrole products
-
2 in the conversion of 3k to 5k (Table 2). Nevertheless, under the conditions described in Scheme 3, substituted isopyrrole products were not detected. We speculate that the additional additives present under these conditions promote the isomerization of ispoyrrole intermediates into the corresponding pyrrole products.
-
-
-
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38
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0348086636
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Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655.
-
(1985)
Tetrahedron.
, vol.41
, pp. 3655
-
-
Wakabayashi, Y.1
Fukuda, Y.2
Shiragami, H.3
Utimoto, K.4
Nozaki, H.5
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