Regioselective synthesis of acyclic cis-enediynes via an acid-catalyzed rearrangement of 1,2-dialkynylallyl alcohols. Syntheses, computational calculations, and mechanism

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5062-5082

  Dai, Wei Min ^a   Wu, Jinlong ^a   Fong, Kin Chiu ^a   Lee, Mavis Yuk Ha ^a   Lau, Chi Wai ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNYL GROUP; ALLYL ALCOHOL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; GENE REARRANGEMENT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0033059723     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982476v     Document Type: Article

References (94)

1. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
2. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
3. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
4. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
5. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
6. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
7. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
8. Selected reviews on chemistry and biology of enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (c) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (d) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (e) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5881. (f) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283. (g) Lhermitte, H.; Grierson, D. S. Comtemp. Org. Synth. 1996, 3, 41 and 93. (h) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
9. (a) Enediynes Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel Dekker: New York, 1994.
10. (b) DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; Kluwer Academic Publishers: Dordrecht, 1996; pp 1-73.
11. Structure of neocarzinostatin chromophore, see: Edo, K.; Mizuyaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331.
12. I, see: Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464. Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
13. I, see: Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464. Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
14. 1, see: Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461. Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkama, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.
15. 1, see: Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461. Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkama, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.
16. Structure of namenamicin, see: McDonald, L. A.; Capson, T. L.; Krishnamurthy, G.; Ding, W.-D.; Ellestad, G. A.; Bernan, V. S.; Maiese, W. M.; Lassota, P.; Discafani, C.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1996, 118, 10898.
17. Structure of dynemicin A, see: Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
18. Structure of dynemicin A, see: Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
19. Structure of kedarcidin chromophore, see: Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson, K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. Revised structure, see: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
20. Structure of kedarcidin chromophore, see: Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson, K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. Revised structure, see: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
21. Structure of kedarcidin chromophore, see: Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946. Leet, J. E.; Schroeder, D. R.; Langley, D. R.; Colson, K. L.; Huang, S.; Klohr, S. E.; Lee, M. S.; Golik, J.; Hofstead, S. J.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1993, 115, 8432. Revised structure, see: Kawata, S.; Ashizawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
22. Structure of C-1027 chromophore, see: Yoshida, K.; Minami, Y.; Azuma, R.; Sakei, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Iida, K.; Ishii, T.; Hirama, M.; Otani, T.; Minami, Y.; Yoshida, K. Tetrahedron Lett. 1993, 34, 4079. Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett. 1996, 37, 4997.
23. Structure of C-1027 chromophore, see: Yoshida, K.; Minami, Y.; Azuma, R.; Sakei, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Iida, K.; Ishii, T.; Hirama, M.; Otani, T.; Minami, Y.; Yoshida, K. Tetrahedron Lett. 1993, 34, 4079. Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett. 1996, 37, 4997.
24. Structure of C-1027 chromophore, see: Yoshida, K.; Minami, Y.; Azuma, R.; Sakei, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637. Iida, K.; Ishii, T.; Hirama, M.; Otani, T.; Minami, Y.; Yoshida, K. Tetrahedron Lett. 1993, 34, 4079. Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett. 1996, 37, 4997.
25. Structure of maduropeptin chromophore, see: Schroeder, D. R.; Colson, K. L.; Klohr, S. E.; Zein, N.; Langley, D. R.; Lee, M. S.; Matson, J. A.; Doyle, T. W. J. Am. Chem. Soc. 1994, 116, 9351.
26. Structure of N1999A2, see: Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Sugiura, Y. Tetrahedron Lett. 1998, 39, 6495.
27. (a) Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660.
28. (b) Bergman, R. G. Acc. Chem. Res. 1973, 6, 25.
29. (c) Lockhart, T. P.; Commita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4082.
30. (d) Lockhart, T. P.; Commita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091.
31. (e) Darby, N.; Kim, C. V.; Salaun, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc., Chem. Commun. 1971, 1516.
32. (f) Wong, H. N. C.; Sondheimer, F. Tetrahedron Lett. 1980, 21, 217.
33. (a) Murphy, J. A.; Griffiths, J. Nat. Prod. Rep. 1993, 551.
34. (b) Pratviel, G. P.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746.
35. (c) Pogozelski, W. K.; Tullius, T. D. Chem. Rev. 1998, 98, 1089.
36. Recent Progress in the Chemistry of Enediyne Antibiotics; Tetrahedron Symposia-in-print No. 53; Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, No. 5.
37. Recent Progress in the Chemistry of Enediyne Antibiotics; Tetrahedron Symposia-in-print No. 53; Doyle, T. W., Kadow, J. F., Eds.; Tetrahedron 1994, 50, No. 5.
38. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
39. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon Press: New York, 1991; Vol. 3, pp 521-549.
40. (a) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771.
41. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
42. (c) Mitchell, T. N. Synthesis 1992, 803.
43. (a) Shair, M. D.; Yoon, T.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755.
44. (b) Shair, M. D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
45. (c) Shair, M. D.; Yoon, T.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721.
46. (d) Shair, M. D.; Yoon, T. Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509.
47. (e) Takahashi, T.; Sakamoto, Y.; Yanada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
48. (f) Tanaka, H.; Yamada, H.; Matsuda, A.; Takahashi, T. Synlett 1997, 381.
49. (g) Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1996, 118, 4904.
50. (h) Nantz, M. H.; Moss, D. K.; Spence, J. D.; Olmstead, M. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 470.
51. Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859.
52. (a) Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805.
53. (b) Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107.
54. (a) Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20.
55. (b) Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469.
56. (c) Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897.
57. (d) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875.
58. (e) Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M. Synlett 1997, 250.
59. (f) Wang, J.; De Clercq, P. J. Angew. Chem., Int. Ed. Engl 1995, 34, 1749.
60. (g) Takahashi, T.; Tanaka, H.; Matsuda, A.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Tetrahedron Lett. 1996, 37, 2433.
61. (h) Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835.
62. (i) Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 1524.
63. (a) Semmelhack, M. F.; Gallagher, J. Tetrahedron Lett. 1993, 34, 4121.
64. (b) Semmelhack, M. F.; Gallagher, J. J.; Ding, W.-D.; Krishnamurthy, G.; Babine, R.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4357.
65. (a) Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1991, 32, 3679.
66. (b) Maier, M. E.; Greiner, B. Liebigs Ann. Chem. 1992, 855.
67. Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35, 37.
68. (a) Dai, W.-M.; Fong, K. C.; Danjo, H.; Nishimoto, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 779.
69. (b) Dai, W.-M.; Fong, K. C. Tetrahedron Lett. 1996, 37, 8413.
70. (c) Dai, W.-M.; Lee, M. Y. H. Tetrahedron Lett. 1998, 39, 8149.
71. (a) Hopf, H.; Theurig, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1099.
72. (b) Hopf, H.; Theurig, M.; Jones, P. G.; Bubenitschek, P. Liebigs Ann. Chem. 1996, 1301.
73. (c) Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110.
74. (d) Bunnage, M. E.; Nicolaou, K. C. Chem. Eur. J. 1997, 3, 187.
75. Review: Maier, M. E. Synlett 1995, 13.
76. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549.
77. Pourcelot, G.; Cadiot, P.; Willemart, A. C. R. Hebd. Seances Acad. Sci. 1961, 252, 1630.
78. Lütjens, H.; Nowotny, S.; Knochel, P. Tetrahedron: Asymmetry 1995, 6, 2675.
79. Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088.
80. (Z)- and (E)-3-(p-Methoxyphenyl)-2-bromo-propenoate, see; Le Menn, J.-C.; Saarrazin, J.; Tallec, A. Can. J. Chem. 1989, 67, 1332. Assignment of the (Z) and (E) isomers seems not correct.
81. (a) Pocker, Y.; Hill, M. J. J. Am. Chem. Soc. 1969, 91, 3243.
82. (b) Pocker, Y.; Hill, M. J. J. Am. Chem. Soc. 1971, 93, 691.
83. Isomerization barrier for allylic cations, see: Bollinger, J. M.; Brinich, J. M.; Olah, G. A. J. Am. Chem. Soc. 1970, 92, 4025.
84. Izawa, K.; Okuyama, T.; Sakagami, T.; Fueno, T. J. Am. Chem. Soc. 1973, 95, 6752.
85. An ion-neutral complex was proposed for intramolecular racemization and regioisomerization of chiral allyl alcohol in the gas phase, see: (a) Troiani, A.; Gasparrini, F.; Graninetti, F.; Speranza, M. J. Am. Chem. Soc. 1997, 119, 4525. (b) Troiani, A.; Speranza, M. J. Org. Chem. 1998, 63, 1012. (c) Speranza, M.; Troiani, A. J. Org. Chem. 1998, 63, 1020.
86. An ion-neutral complex was proposed for intramolecular racemization and regioisomerization of chiral allyl alcohol in the gas phase, see: (a) Troiani, A.; Gasparrini, F.; Graninetti, F.; Speranza, M. J. Am. Chem. Soc. 1997, 119, 4525. (b) Troiani, A.; Speranza, M. J. Org. Chem. 1998, 63, 1012. (c) Speranza, M.; Troiani, A. J. Org. Chem. 1998, 63, 1020.
87. An ion-neutral complex was proposed for intramolecular racemization and regioisomerization of chiral allyl alcohol in the gas phase, see: (a) Troiani, A.; Gasparrini, F.; Graninetti, F.; Speranza, M. J. Am. Chem. Soc. 1997, 119, 4525. (b) Troiani, A.; Speranza, M. J. Org. Chem. 1998, 63, 1012. (c) Speranza, M.; Troiani, A. J. Org. Chem. 1998, 63, 1020.
88. Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16. Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1994, 66, 201. Brown, H. C.; Ramachandran, P. V. Organomet. Chem. 1995, 500, 1. Dhar, R. K. Aldrichimica Acta 1994, 27, 43.
89. Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16. Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1994, 66, 201. Brown, H. C.; Ramachandran, P. V. Organomet. Chem. 1995, 500, 1. Dhar, R. K. Aldrichimica Acta 1994, 27, 43.
90. Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16. Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1994, 66, 201. Brown, H. C.; Ramachandran, P. V. Organomet. Chem. 1995, 500, 1. Dhar, R. K. Aldrichimica Acta 1994, 27, 43.
91. Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16. Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1994, 66, 201. Brown, H. C.; Ramachandran, P. V. Organomet. Chem. 1995, 500, 1. Dhar, R. K. Aldrichimica Acta 1994, 27, 43.
92. Ramachandran, P. V.; Teodorovic, A. V.; Rangaishenvi, M. V.; Brown, H. C. J. Org. Chem. 1992, 57, 2379.
93. Dai, W.-M.; Fong, K. C.; Lau, C. W.; Zhou, L.; Hamahuchi, W.; Nishimoto, S. J. Org. Chem. 1999, 64, 682.
94. Gaussian 94, Revision D. 3; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1995.