Substituted diether diols by ring-opening of carbocyclic and stannylene acetals

Tetrahedron

Volumn 54, Issue 31, 1998, Pages 8919-8932

  Martínez Bernhardt, Rolando ^a   Castro, Peter P ^a   Godjoian, Gayane ^a   Gutiérrez, Carlos G ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIBROMOETHANE; 2 CHLOROETHANOL; ACETAL DERIVATIVE; BORANE DERIVATIVE; ETHER DERIVATIVE; GLYOXAL DERIVATIVE; MALONALDEHYDE; TRIETHYLENE GLYCOL;

ALKYLATION; ARTICLE; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0032581603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00563-8     Document Type: Article

References (74)

1. 1. Gokel, G.W.; Korzeniowski, S.H. Macrocyclic Polyether Syntheses; Springer-Verlag, New York, 1982.; Crown Compounds: Toward Future Applications; Cooper, S.R. Ed.; VCH, New York, 1992, Zhang, X.X.; Bradshaw, J.S.; Izatt, R.M. Chem. Rev. 1997, 97, 3313.
2. 1. Gokel, G.W.; Korzeniowski, S.H. Macrocyclic Polyether Syntheses; Springer-Verlag, New York, 1982.; Crown Compounds: Toward Future Applications; Cooper, S.R. Ed.; VCH, New York, 1992, Zhang, X.X.; Bradshaw, J.S.; Izatt, R.M. Chem. Rev. 1997, 97, 3313.
3. 1. Gokel, G.W.; Korzeniowski, S.H. Macrocyclic Polyether Syntheses; Springer-Verlag, New York, 1982.; Crown Compounds: Toward Future Applications; Cooper, S.R. Ed.; VCH, New York, 1992, Zhang, X.X.; Bradshaw, J.S.; Izatt, R.M. Chem. Rev. 1997, 97, 3313.
4. 2. Voegtle, F.; Weber, E. Host-Guest Chemistry/Macrocycles; Springer Verlag: New York, 1985.
5. 3. Izatt, R.M.; Christiansen, J.J. Eds. Synthesis of Macrocycles: The Design of Selective Complexing Agents; Wyley-Interscience: New York, 1987.
6. 4. Dyer, B.R.; Metcalf, D.H.; Ghirardelli, R.G.; Palmer, R.A.; Holt, E.M. J. Am. Chem. Soc. 1986, 108, 3621.
7. 5. a) Dutton, P.J.; Fyles, T.M.; McDermid, S. Can. J. Chem. 1988, 66, 1097;
8. b) Fyles, T.M. ; Kaye K.C.; James, T.D.; Smiley, D.W.M. Tetrahedron Lett. 1990, 1233;
9. c) Carmichael, V.E.; Dutton, P.J.; Fyles, T.M.; James, T.D.; Swan, J.A.; Zojaji, M. J. Am. Chem. Soc. 1989, 111, 767;
10. d) Sasaki, S.; Koga, K. Heterocycles 1979, 12, 1305.
11. 6. Preliminary reports of parts of this work have been made: a) Castro, P.P.; Tihomirov, S.; Gutierrez, C. J. Org. Chem. 1988, 53, 5179;
12. b) Godjoian, G.; Wang, V.R.; Ayala, A.M.; Martínez, R. V.; Martínez-Bernhardt, R.; Gutiérrez, C.G. Tetrahedron Lett. 1996, 433.
13. 7. Chastrette, F.; Hassambay, M.; Chastrette, M. Bull. Soc. Chim. Fr. 1976, 601.
14. 4-Lewis Acids: Eliel, E.; Badding, V.G.; Rerick, M.N. J. Am. Chem. Soc. 1962, 84, 2371. Joniak, D.; Kosikova, B.; Kosakova, L. Coll. Czech. Chem. Commun. 1978, 43, 769. Ishikawa, H.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1978, 51, 2059.
15. 4-Lewis Acids: Eliel, E.; Badding, V.G.; Rerick, M.N. J. Am. Chem. Soc. 1962, 84, 2371. Joniak, D.; Kosikova, B.; Kosakova, L. Coll. Czech. Chem. Commun. 1978, 43, 769. Ishikawa, H.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1978, 51, 2059.
16. 4-Lewis Acids: Eliel, E.; Badding, V.G.; Rerick, M.N. J. Am. Chem. Soc. 1962, 84, 2371. Joniak, D.; Kosikova, B.; Kosakova, L. Coll. Czech. Chem. Commun. 1978, 43, 769. Ishikawa, H.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1978, 51, 2059.
17. 3-THF: Fleming, B.; Bolker, H.I Can. J. Chem. 1974, 52, 889; Can. J. Chem. 1977, 53, 2818.
18. 3-THF: Fleming, B.; Bolker, H.I Can. J. Chem. 1974, 52, 889; Can. J. Chem. 1977, 53, 2818.
19. 2Cl: Bonner, T.G.; Lewis, D.; Rutter, K. J. Chem. Soc. Perkin Trans. I 1981, 1807.
20. 2 over catalysts: Fleming, B.; Bolker, H.I Can. J. Chem. 1976, 54, 685; Howard, W.L.; Brown, J.H. J. Org. Chem. 1961, 26, 1026.
21. 2 over catalysts: Fleming, B.; Bolker, H.I Can. J. Chem. 1976, 54, 685; Howard, W.L.; Brown, J.H. J. Org. Chem. 1961, 26, 1026.
22. 4-HCl: Horne, D.A.; Jordan, A. Tetrahedron Lett. 1978, 1357. Kloosterman, M.; Kuyl-Yeheskiely, E.; van Boom, J.H. Recl. Trav. Chim. Pays-Bos 1985, 104, 291.
23. 4-HCl: Horne, D.A.; Jordan, A. Tetrahedron Lett. 1978, 1357. Kloosterman, M.; Kuyl-Yeheskiely, E.; van Boom, J.H. Recl. Trav. Chim. Pays-Bos 1985, 104, 291.
24. 3COOH: Nutaitis, C.F.; Gribble, G. W. Org Prep. Proc. Int. 1985, 17, 11.
25. 3Cl: Kotsuki, H; Ushio, Y.; Yoshimura, N.; Ochi, M. J. Org. Chem. 1987, 52, 2594.
26. 3SiH: Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 4679. Olah, G.A.; Yamato, T.; Iyer, P.S.; Surya Prakash, G.K. J. Org. Chem. 1986, 51, 2826. Doyle, M.P.; DeBruyn, D.J.; Kooistra, D.A. J. Am. Chem. Soc. 1972, 94, 3659.
27. 3SiH: Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 4679. Olah, G.A.; Yamato, T.; Iyer, P.S.; Surya Prakash, G.K. J. Org. Chem. 1986, 51, 2826. Doyle, M.P.; DeBruyn, D.J.; Kooistra, D.A. J. Am. Chem. Soc. 1972, 94, 3659.
28. 3SiH: Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 4679. Olah, G.A.; Yamato, T.; Iyer, P.S.; Surya Prakash, G.K. J. Org. Chem. 1986, 51, 2826. Doyle, M.P.; DeBruyn, D.J.; Kooistra, D.A. J. Am. Chem. Soc. 1972, 94, 3659.
29. (i) Diisobutylaluminum hydride: Schill, G.; Doejer, G.; Longemann, E.; Vetter, W. Chem. Ber. 1980, 113, 3697.
30. 2H: Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1983, 4581.
31. 3: Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004,
32. 3: Ghribi, A.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1984, 3075, 3079.
33. (m) TiCl4 and organosilanes: Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088. Lindell, S.D.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 3947, 3951. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. J. Org. Chem. 1983, 48, 2294. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. Tetrahedron Lett. 1984, 591.
34. (m) TiCl4 and organosilanes: Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088. Lindell, S.D.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 3947, 3951. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. J. Org. Chem. 1983, 48, 2294. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. Tetrahedron Lett. 1984, 591.
35. (m) TiCl4 and organosilanes: Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088. Lindell, S.D.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 3947, 3951. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. J. Org. Chem. 1983, 48, 2294. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. Tetrahedron Lett. 1984, 591.
36. (m) TiCl4 and organosilanes: Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088. Lindell, S.D.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 3947, 3951. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. J. Org. Chem. 1983, 48, 2294. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. Tetrahedron Lett. 1984, 591.
37. (m) TiCl4 and organosilanes: Bartlett, P.A.; Johnson, W.S.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088. Lindell, S.D.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 3947, 3951. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. J. Org. Chem. 1983, 48, 2294. Elliot, J.D.; Choi, V.M.F.; Johnson, W.S. Tetrahedron Lett. 1984, 591.
38. 3: Mori, A.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1984, 4421.
39. 3SiI: Bryant, J.D.; Keyzer, G.E.; Barrio, J.R. J. Org. Chem. 1979, 44, 3733.
40. 9. Guindon, Y.; Therien, M.; Girard, Y. Yoakim, C. J. Org. Chem. 1987, 52, 1680.
41. 10. Schmidt, K.; O'Neal, S.; Chan, T.C.; Alexis, C.P.; Uribe, J.M.; Lossener, K.; Gutierrez, C.G. Tetrahedron Lett. 1989, 7301.
42. 11. Alexis, C.P.; Uribe, J.M.; Beller, J.D.; Godjoian, G.; Gutierrez, C.G. Phosphorous, Sulfur and Silicon 1996, 1, 93.
43. 12. Sprung, M.M.; Guenther, F.O. J. Am. Chem. Soc. 1951, 73, 1884.
44. 3) observed in unambiguous compounds: 6 (4.95 ppm) and 9 (4.45 ppm); 8 (5.15 ppm) and 11 (4.85 ppm). Extending this, we assigned the absorbance at 4.74 ppm to the acetal methine protons in tetramethylbidioxolane 32, and the resonance at 4.43 to those on tetramethyltetraoxadecalin 33; and 4.55 ppm for octamethylbidioxolane 34 and 4.11 ppm for the octamethyltetraoxadecalin 35.
45. 14. Gandour, R.D.; Fronczek, F.R.; Gatto, V.J.; Mignanti, C.; Schultz, R.A.; White, B.D.; Arnold, K.A.; Mazzochi, D.; Miller, S.R.; Gokel, G.W.; J. Am. Chem. Soc. 1986, 108, 4078.
46. 15. Deslongchamps, P. "Stereoelectronic Effects in Organic Chemistry"; Pergamon Press: New York, 1983; p 5.
47. 16 Mori, A.; Fujiwara, J.; Marouka, K.; and Yamamoto, H.; Tetrahedron Lett. 1983, 24, 4581.
48. 17. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis, Butterworths, Boston, 1987, pp. 269-277; McKervey, M.A.; O'Connor, T. J. Chem. Soc. Chem. Commun. 1982, 655.
49. 17. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis, Butterworths, Boston, 1987, pp. 269-277; McKervey, M.A.; O'Connor, T. J. Chem. Soc. Chem. Commun. 1982, 655.
50. 18. David, S.; Hannessian, S. Tetrahedron 1985, 41, 663.
51. 19. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
52. 19. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
53. 19. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
54. 19. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
55. 20. Nagashima, N.; Ohno, M. Chem. Lett. 1987, 141; Nagashima, N.; Ohno, M. Chem. Pharm. Bull 1991, 39, 1972.
56. 20. Nagashima, N.; Ohno, M. Chem. Lett. 1987, 141; Nagashima, N.; Ohno, M. Chem. Pharm. Bull 1991, 39, 1972.
57. 21. For comparison with the organotin methodology presented here, reaction of the potassium or sodium alkoxide of diol 3b with dibromoethane resulted largely in elimination products.
58. 22. Tor, Y.; Libman, J.; Shanzer, A.; Lifson, S. J. Am. Chem. Soc. 1987, 109, 6517.
59. 23. a) The formation of dioxane from the reaction of dibromoethane and the stannylene acetal derived from ethylene glycol has been previously observed: Pommier, J.-C; Valade, J. C. R. Acad. Sc. (Paris) 1965, 4549;
60. b) The formation of 2,3-dimethyl-1,4-dioxane has been reported from ethylene glycol bis(tributylstannyl) ether and dibromoethane: Ratier, M.; Delmond, B.; Pommier, J.-C. Bull. Soc. Chim. Fr. 1972, 1593.
61. 24. For examples of internal alkylation of haloalkyltributyltinalkoxides to form oxygen heterocycles: Delmond, B.; Pommier, J.-C.; Valade, J. J. Organometallic. Chem. 1972, 35, 91; Odeh, A.M.S.; Usta, J.A.; Issidorides, C.H. Heterocycles 1980, 189.
62. 24. For examples of internal alkylation of haloalkyltributyltinalkoxides to form oxygen heterocycles: Delmond, B.; Pommier, J.-C.; Valade, J. J. Organometallic. Chem. 1972, 35, 91; Odeh, A.M.S.; Usta, J.A.; Issidorides, C.H. Heterocycles 1980, 189.
63. 25. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
64. 25. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
65. 25. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
66. 25. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
67. 26. Dialkylation of the stannylene acetal of 2,2-dimethyl-1,3-propanediol with a bromoacetamide at toluene reflux has been reported: Shanzer, A.; Samuel, D.; Korenstein, R. J. Am. Chem. Soc. 1983, 105, 3815.
68. 27. Still, W.C; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
69. 28. Conveniently done on a Harrison Research (Palo Alto, CA) Chromatotron.
70. 29. Rosen, W.; Busch, D.H. J. Am. Chem. Soc. 1969, 91, 4694.
71. 30. The reported melting point for the meso isomer is 124-126° (C. Considine J. Organometallic Chem, 1966, 5, 263). We have found that the melting point of the racemic modification is 141-142 °C, and the (S,S)-enantiomer is 134 °C.
72. 31. Nagashima, N.; Ohno, M. Chem. Lett. 1987, 141; Nagashima, N.; Ohno, M. Chem. Pharm. Bull. 1991, 39, 1972.
73. 31. Nagashima, N.; Ohno, M. Chem. Lett. 1987, 141; Nagashima, N.; Ohno, M. Chem. Pharm. Bull. 1991, 39, 1972.
74. 32. Mash, E.A.; Nelson, K.A.; Van Deusen, S.; Hemperley, S.B. Org. Synth. 1989, 68, 92.