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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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Tetrahedron Lett.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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Honda, T.1
Namiki, H.2
Satoh, F.3
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For related Pd-catalyzed intramolecular coupling of aryl halides and ketone enolates, see: (a) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. (b) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. (c) Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439. (d) Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888. (e) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. For Pd-catalyzed intramolecular coupling of aryl halides and amide enolates, see: (f) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546. (g) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402. (h) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247. (i) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193. (j) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363. (k) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631. For a Pd-catalyzed intramolecular coupling of aryl halides and α-amino acid esters, see: (l) Gaertzen O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465.
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Gaertzen, O.1
Buchwald, S.L.2
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65
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0038738319
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note
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The formation of deallylated products has also been reported by Cook.
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66
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84960070165
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In fact, all indole alkaloids bearing a 20-ethylidene side chain in the piperidine ring shows an E configuration: Bosch, J.; Bennasar, M. L. Heterocycles 1983, 20, 2471.
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Bosch, J.1
Bennasar, M.L.2
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84989052512
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Casamitjana, N.; Bonjoch, J.; Gràcia, J.; Bosch, J. Magn. Reson. Chem. 1992, 30, 183.
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Casamitjana, N.1
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Gràcia, J.3
Bosch, J.4
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69
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0038061890
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note
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The isomerization of the initially formed annulation products to the conjugated enones under the reaction condition was also observed by Piers.
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70
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0038400170
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note
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3 was used as the base.
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71
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0025959497
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For easy air oxidation of 3-acylpirrolines to 3-acylpyrroles, see: Chou, S.-S. P.; Yuan, T.-M. Synthesis 1991, 171.
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Synthesis
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Chou, S.-S.P.1
Yuan, T.-M.2
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0038738318
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note
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13C NMR spectra of this compound were unambiguously assigned with the aid of 2D-NMR experiments (COSY and HSQC) and NOESY.
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