Molybdenum(IV) complexes as efficient, Lewis acidic catalysts for allylic substitution. Formation of C-C and C-N bonds

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5308-5311

  Malkov, Andrei V ^a   Spoor, Paul ^a   Vinader, Victoria ^b   Kočovský, Pavel ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALLYL COMPOUND; CARBONIC ACID; LIGAND; MALONIC ACID; MOLYBDENUM; TUNGSTEN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; ENVIRONMENTAL TEMPERATURE; POLYMERIZATION; REPRODUCIBILITY; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0033067091     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990372u     Document Type: Article

References (74)

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34. 2, which gave a 1:1 mixture of o- and p-(2-cyclohexen-1-yl)phenols (75%) at ambient temperature in 30 min.
35. 5e
36. 2 (rt, 1 h), which gave (±)-3-methoxy-1-phenyl-1-butene.
37. The yield is based on 9 and is rather low in this case owing to the competing elimination and polymerization. More than 60% of the unreacted 11 has been detected in the crude reaction mixture.
38. -, which renders Mo-(IV) unreactive.
39. 3 in the Pd(0)-catalyzed allylic substitution, see: Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485.
40. In this case, the relatively low isolated yield is due to the high volatility of the product.
41. Note that treatment of 10 with HBr is a preparative method to make prenyl bromide: Tietze, L.-F.; Eicher, T. Reaktionen und Synthesen im organisch-chemischen Praktikum; G. Thieme: Stuttgart, 1981; p 42.
42. 1H NMR spectrum of the crude mixture. For further details, see: Ortar, G.; Paradisi, M. P.; Morera, E.; Romeo, A. J. Chem. Soc., Perkin Trans. 1 1978, 4.
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46. 6: (a) Wenkert, E.; Fernandes, J. B.; Michelott, E. L.; Swindell, C. S. Synthesis 1983, 701. (b) Dewar, M. J. S.; Nahlovsky, B. D. J. Am. Chem. Soc. 1974, 96, 460. and 8: Reference 5f. 12: (c) Bunina- Krivorukova, L. I.; Feoktistov, V. M.; Aleksandrova, E. K.; Bal'yan, Kh. V. Zh. Org. Khim. 1982, 18, 859. (d) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487. (e) De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagliano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993. 13: Reference 18c,d. (h) Baird, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1980, 1820. 15: (f) Ballester, P.; Capo, M.; Saa, J. M. Tetrahedron Lett. 1990, 31, 1339. (g) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
47. 6: (a) Wenkert, E.; Fernandes, J. B.; Michelott, E. L.; Swindell, C. S. Synthesis 1983, 701. (b) Dewar, M. J. S.; Nahlovsky, B. D. J. Am. Chem. Soc. 1974, 96, 460. and 8: Reference 5f. 12: (c) Bunina- Krivorukova, L. I.; Feoktistov, V. M.; Aleksandrova, E. K.; Bal'yan, Kh. V. Zh. Org. Khim. 1982, 18, 859. (d) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487. (e) De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagliano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993. 13: Reference 18c,d. (h) Baird, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1980, 1820. 15: (f) Ballester, P.; Capo, M.; Saa, J. M. Tetrahedron Lett. 1990, 31, 1339. (g) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
48. 6: (a) Wenkert, E.; Fernandes, J. B.; Michelott, E. L.; Swindell, C. S. Synthesis 1983, 701. (b) Dewar, M. J. S.; Nahlovsky, B. D. J. Am. Chem. Soc. 1974, 96, 460. and 8: Reference 5f. 12: (c) Bunina- Krivorukova, L. I.; Feoktistov, V. M.; Aleksandrova, E. K.; Bal'yan, Kh. V. Zh. Org. Khim. 1982, 18, 859. (d) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487. (e) De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagliano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993. 13: Reference 18c,d. (h) Baird, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1980, 1820. 15: (f) Ballester, P.; Capo, M.; Saa, J. M. Tetrahedron Lett. 1990, 31, 1339. (g) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
49. 6: (a) Wenkert, E.; Fernandes, J. B.; Michelott, E. L.; Swindell, C. S. Synthesis 1983, 701. (b) Dewar, M. J. S.; Nahlovsky, B. D. J. Am. Chem. Soc. 1974, 96, 460. and 8: Reference 5f. 12: (c) Bunina- Krivorukova, L. I.; Feoktistov, V. M.; Aleksandrova, E. K.; Bal'yan, Kh. V. Zh. Org. Khim. 1982, 18, 859. (d) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487. (e) De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagliano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993. 13: Reference 18c,d. (h) Baird, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1980, 1820. 15: (f) Ballester, P.; Capo, M.; Saa, J. M. Tetrahedron Lett. 1990, 31, 1339. (g) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
50. 6: (a) Wenkert, E.; Fernandes, J. B.; Michelott, E. L.; Swindell, C. S. Synthesis 1983, 701. (b) Dewar, M. J. S.; Nahlovsky, B. D. J. Am. Chem. Soc. 1974, 96, 460. and 8: Reference 5f. 12: (c) Bunina- Krivorukova, L. I.; Feoktistov, V. M.; Aleksandrova, E. K.; Bal'yan, Kh. V. Zh. Org. Khim. 1982, 18, 859. (d) Julia, M.; Nel, M.; Uguen, D. Bull. Soc. Chim. Fr. 1987, 487. (e) De Renzi, A.; Panunzi, A.; Saporito, A.; Vitagliano, A. J. Chem. Soc., Perkin Trans. 2 1983, 993. 13: Reference 18c,d. (h) Baird, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1980, 1820. 15: (f) Ballester, P.; Capo, M.; Saa, J. M. Tetrahedron Lett. 1990, 31, 1339. (g) Araki, S.; Manabe, S.; Butsugan, Y. Chem. Lett. 1982, 797.
51. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
52. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
53. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
54. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
55. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
56. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
57. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
58. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
59. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
60. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
61. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
62. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
63. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
64. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
65. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
66. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
67. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
68. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
69. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
70. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
71. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
72. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
73. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
74. 16 (E): (a) Manhart, E.; von Werner, K. Synthesis 1978, 705. (b) Hassner, A.; Fibiger, R.; Andisik, D. J. Org. Chem. 1984, 49, 4237. (c) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. (d) Viaud, M. C.; Rollin, P. Synthesis 1990, 130. (e) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (f) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (g) Blart, E.; Genet, J.-P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505. (h) Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413. (i) Rosen, T.; Lico, I. M.; Chu, D. T. W. J. Org. Chem. 1988, 53, 1580. (E/Z): (j) Balderman, D.; Kalir, A. Synthesis 1978, 24. (k) Yang, C.-H.; Shen, H.-J. Tetrahedron Lett. 1993, 34, 4051. (l) Koriara, A.; Zwierzak, A. Synthesis 1992, 1063. (E): (m) Murahashi, S.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292. 19: (n) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274. (o) Banert, K.; Groth, S. Angew. Chem. 1992, 104, 865. 22: (p) Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165. (q) Breton, G. W.; Daus, K. A.; Kropp, P. J. J. Org. Chem. 1992, 57, 6646. 23: (r) Grieco, P. A.; DuBay, W. J.; Todd, L. J. Tetrahedron Lett. 1996, 37, 8707. (s) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645. 25: (t) Hassner, A.; Fowler, F. W. J. Org. Chem. 1968, 33, 2684. (u) Blond, A.; Platzer, N.; Guy, A.; Dhotel, H.; Serva, L. Bull. Soc. Chim. Fr. 1996, 133, 283. (v) Chmielowiec, U.; Uzarewicz, I.; Uzarewicz, A. Pol. J. Chem. 1990, 64, 613. (x) Hassner; Fowler, F. J. Org. Chem. 1968, 33, 2684, 2686. 28: Reference 17. 29: Reference 17. (y) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.