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For a review, see: H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977.
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For catalytic asymmetric intermolecular cyclopropanation reactions, see: a) B. Moreau, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 18 014;
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e) V. K. Aggarwal, E. Alonso, G. Hynd, K. M. Lydon, M. J. Palmer, M. Porcelloni, J. R. Studley, Angew. Chem. 2001, 113, 1482;
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0038081446
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For examples of catalytic intramolecular cyclopropanation strategies, see: a) A. Fürstner, H. Szilat, F. Steltzer, J. Am. Chem. Soc. 2000, 122, 6785;
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3242713858
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b) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriers, A. L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 726, 8656;
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4444291533
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c) M. R. Luzung, J. P. Markham, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 10 858;
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d) D. Yang, Q. Gao. C.-S. Lee, K.-K. Cheung, Org. Lett. 2002, 4, 3271;
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Yang, D.1
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33644660502
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e) T. Miura, T. Sasaki, T. Harumashi, M. Murakami, J. Am. Chem. Soc. 2006, 128, 2516.
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Miura, T.1
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0037433496
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b) M. Honma, T. Sawada, Y. Fujisawa, M. Utsugi, H. Watanabe, A. Umino, T. Matsumura, T. Hagihara, M. Takano, M. Nakada, J. Am. Chem. Soc. 2003, 125, 2860;
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20
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0000100584
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c) it is also possible to form [n.1.0]-bicyclic motifs through the intermolecular cyclopropanation of cyclic alkenes; for examples, see: M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911.
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0242574862
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For examples of using strain-driven reactivity, see: a) R. Sarpong, J. T. Su, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 13 624;
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b) P. A. Wender, C. O. Husfild, E. Langkopf, J. Love, J. Am. Chem. Soc. 1998, 120, 1940.
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a) N. Bremeyer, S. C. Smith, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 2735;
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33748765403
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note
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a) Based on LC-mass-spectrometric analysis of the mixture; b) quinoline A, when treated with 1 a and NaBr in MeCN at 80°C, leads to an intractable mixture of products and consumes all the starting material; quinoline B does not react with 1 a under the same conditions, thus both materials are returned untouched; no cyclopropanantion was observed in these reactions.
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26
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0348224168
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1′-deazo cinchona alkaloids have been synthesized previously through a nontrivial route: a) C. Exner, A. Pfaltz, M. Studer, H.-U. Blaser, Adv. Synth. Catal. 2003, 345, 1253;
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b) E. V. Dehmlow, S. Düttmann, B. Neumann, H.-G. Stammler, Eur. J. Org. Chem. 2002, 2087.
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Dehmlow, E.V.1
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Neumann, B.3
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28
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33748764532
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note
-
We also tested catalysts containing C2′-Ph (83 % yield, 96 % ee), iPr (59% yield, 98% ee), and tBu (46% yield, 93% ee), but the Me-MQ/ Me-MQD catalysts gave the best results.
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29
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33748809670
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See the Supporting Information for details
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See the Supporting Information for details.
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30
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0034620689
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For isolation, see: a) S. F. Brady, M. P. Singh, J. E. Janso, J. Clardy, J. Am. Chem. Soc. 2000, 122, 2116;
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31
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for the first synthesis, see: b) S. Lin, G. S. Dudley, D. S. Tan, S. J. Danishevsky, Angew. Chem. 2002, 114, 2292;
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P. Ramesh, N. Srinivasa, Y. Venkateswarlu, M. V. R. Reddy, D. J. Faulkner, Tetrahedron Lett. 1998, 39, 8217.
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Faulkner, D.J.5
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34
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0012083781
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For a related example of intramolecular [5+2] cycloadditions, see: a) B. M. Trost, H. C. Shen, Angew. Chem. 2001, 113, 2375-2378;
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0035907913
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Angew. Chem. Int. Ed. 2001, 40, 2313-2316;
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Angew. Chem. Int. Ed.
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36
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17444380855
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b) B. M. Trost, H. C. Shen, D. B. Horne, F. D. Toste, B. G. Steinmetz, C. Koradin, Chem. Eur. J. 2005, 11, 2577;
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Koradin, C.6
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37
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0035963703
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and references therein
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see also: c) P. A. Wender, F. C. Bi, M. A. Brodney, F. Gosselin, Org. Lett. 2001, 3, 2105, and references therein.
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Wender, P.A.1
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Gosselin, F.4
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39
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33748783211
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note
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The chloroketone precursors are made through an alkene cross metathesis reaction using the Grubbs second generation catalyst.
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