A Powerful New Strategy for Diversity-Oriented Synthesis of Pyrroles from Donor-Acceptor Cyclopropanes and Nitriles

Organic Letters

Volumn 5, Issue 26, 2003, Pages 5099-5101

  Yu, Ming ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; NITRILE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; CYCLOPROPANATION; DEHYDRATION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0346025399     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036180+     Document Type: Article

References (66)

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17. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
18. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
19. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
20. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
21. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
22. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
23. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
24. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
25. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
26. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
27. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
28. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
29. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
30. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
31. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
32. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
33. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
34. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
35. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
36. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
37. For some contemporary examples, see: (a) Martinez, G. R.; Grieco, P. A.; Srivivasan, C. V. J. Org. Chem. 1981, 46, 3760-3761. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650. (c) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624-625. (d) Barton, D. H. R.; Zard, S. Z. Chem. Commun. 1985, 1098-100. (e) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288. (f) Katrizky, A. R. ; Hitchings, G. J.; Zhao, X. Synthesis 1991, 863-7. (g) Van Leusen, D.; Van Echten, E.; Van Leusen, A. M. J. Org. Chem. 1992, 57, 2245-9. (h) Winkler, J. D.; Siegel, M. G. Tetrahedron Lett. 1993, 34, 7697-700. (i) Trofimov, B. A.; Mikhaleva, A. I. Heterocycles 1994, 37, 1193-232. (j) Chan, W. H.; Lee, A. W. M.; Lee, K. M.; Lee, T. Y. J. Chem. Soc., Perkin Trans. 1 1994, 2355-2356. (k) QuicletSire, B.; Thevenot, I.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 9469-9470. (l) Curran, T. P.; Keaney, M. T. J. Org. Chem. 1996, 61, 9068-9069. (m) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003. (n) Meyers, A. I.; Warmus, J. S.; Dilley, G. Org. Synth. 1996, 73, 246-252. (o) Grigg, R.; Savic, V. Chem. Commun. 2000, 873-874. (p) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819-8821. (q) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. (r) Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Lett. 2001, 3, 421-424. (s) Braun, R. U.; Zeitler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297-3300. (t) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215. (u) Hover, J. A.; Bock, C. W.; Bhat, K. L. Heterocycles 2003, 60, 791-798.
38. Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122-8123.
39. Meyers, A. I.; Sircar, J. C. In The Chemistry of the Cyano Group; Rapporport, Z., Ed.; John Wiley: Belfast, 1970; Chapter 8.
40. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
41. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
42. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
43. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
44. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
45. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
46. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
47. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
48. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
49. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
50. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
51. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
52. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
53. Donor-acceptor cyclopropane reviews: (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72. (b) Wenkert, E. Acc. Chem. Res. 1980, 13, 27-31. (c) Paquette, L. A. Chem. Rev. 1986, 86, 733-750. (d) Reissig, H.-U. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 1987; Chapter 8, pp 375-443. (e) Reissig, H. U. Top. Curr. Chem. 1988, 144, 73-135. (f) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198. (g) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (h) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839-850. (i) Carbocyclic Three-and Four-Membered Ring Compounds. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; de Meijere, A., Ed.; Thieme Verlag: Stuttgart, 1997; Vol. E17a, E17b, E17c, E17d. (j) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67. (k) de Meijere, A.; Kozhushkov, S. I.; Khlebnikow, A. F. Top. Curr. Chem. 2000, 207, 89-147. (l) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. P. Top. Curr. Chem. 2000, 207, 149-227. (m) Reissig, H. Y.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196. (n) Gnad, F.; Reiser O. Chem. Rev. 2003, 103, 1603-1624.
54. Dipolar cycloaddition reviews: (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984. (b) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1111. (c) A. Padwa, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1069. (d) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002.
55. Dipolar cycloaddition reviews: (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984. (b) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1111. (c) A. Padwa, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1069. (d) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002.
56. Dipolar cycloaddition reviews: (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984. (b) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1111. (c) A. Padwa, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1069. (d) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002.
57. Dipolar cycloaddition reviews: (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984. (b) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1111. (c) A. Padwa, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1069. (d) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002.
58. Yu. M.; Lynch, V.; Pagenkopf, B. L. Org. Lett. 2001, 3, 2563-2566.
59. The vinyl ethers were readily prepared by the method of Gassman: (a) Gassman, P. G.; Burns, S. J. J. Org. Chem. 1988, 53, 5574-5576. (b) Gassman, P. G.; Burns, S. J.; Pfister, K. B. J. Org. Chem. 1993, 58, 1449-1457.
60. The vinyl ethers were readily prepared by the method of Gassman: (a) Gassman, P. G.; Burns, S. J. J. Org. Chem. 1988, 53, 5574-5576. (b) Gassman, P. G.; Burns, S. J.; Pfister, K. B. J. Org. Chem. 1993, 58, 1449-1457.
61. For activation with Lewis acids, see: (a) Yu, M.; Lynch, V.; Pagenkopf, B. L. Tetrahedron 2003, 59, 2765-2771. (b) Reference 17.
62. For activation with Lewis acids, see: (a) Yu, M.; Lynch, V.; Pagenkopf, B. L. Tetrahedron 2003, 59, 2765-2771. (b) Reference 17.
63. 3, extracted and purified by chromatography.
64. For a review: Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1998, 615-628.
65. For a recent example: Hodges, L. M.; Spera, M. L.; Moody, M. W.; Harman, W. D. J. Am. Chem. Soc. 1996, 118, 7117-7127.
66. A notable difference in reactivity with those substrates prepared by intramolecular cyclopropanation is that under the standard reaction conditions the 3,4-dihydro-2H-pyrroles 4 can be isolated, but treating them during workup or in a separate step with aqueous acid affords the pyrrole in high yield.