The Paternò-Büchi reaction of 3-heteroatom-substituted alkenes as a stereoselective entry to polyfunctional cyclic and acyclic molecules

Liebigs Annales

Volumn , Issue 8, 1997, Pages 1627-1634

  Bach, Thorsten ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Amino alcohols; Diols; Oxetanes; Photochemistry; Synthetic methods

Indexed keywords

EID: 33748717507     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970803     Document Type: Review

References (79)

1. [1a] M. Bartók, K. L. Láng in Small Ring Heterocycles (Ed.: A. Hassner), Wiley, New York, 1985, part 3, pp. 1-196.
2. [1b] E. G. Lewars in Comprehensive Heterocyclic Chemistry (Ed.: A. R. Katritzky), Pergamon Press, Oxford, 1984, vol. 7, pp. 96-129.
3. [2a] Enantioselective epoxidation of allylic alcohols: R. A. Johnson, K. B. Sharpless, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 103-158.
4. [2b] Enantioselective epoxidation of unfunctionalized alkenes: E. N. Jacobsen, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 159-202.
5. Reviews: [3a] K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38-69;
6. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-43.
7. [3b] A. N. Boa, P. R. Jenkins, N. J. Lawrence, Contemp. Org. Synth. 1994, 47-75.
8. D. G. I. Kingston, Pharm. Ther. 1991, 52, 1-34.
9. N. Shimada, S. Hasegawa, T. Harada, T. Tomisawa, T. Fujii, T. Takita, J. Antibiot. 1986, 39, 1623-1625.
10. S. Omura, M. Murata, N. Imamura, Y. Iwai, H. Tanaka, A. Furusaki, T. Matsumoto, J. Antibiot. 1984, 37, 1324-1332.
11. [7a] S. Searles in The Chemistry of Heterocyclic Compounds (Ed.: A. Weissberger), Wiley-Interscience, New York, 1964, vol. 19-2, pp. 983-1068.
12. [7b] S. Searles in Comprehensive Heterocyclic Chemistry (Ed.: A. R. Katritzky), Pergamon Press, Oxford, 1984, vol. 7, pp. 363-402.
13. Recent reviews: [8a] J. Mattay, R. Conrads, R. Hoffmann in Methoden der Organischen Chemie (Houben-Weyl) 4te Aufl. (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, Band E 21c, pp. 3133-3178.
14. [8b] J. A. Porco, S. L. Schreiber in Comprehensive Organic Synthesis (Ed.: B. Trost), Pergamon Press, Oxford, 1991, vol. 5, pp. 151-192.
15. [8c] H. A. J. Carless in Synthetic Organic Photochemistry (Ed.: W. M. Horspool), Plenum Press, New York, 1984, pp. 425-487.
16. [8d] G. Jones II in Organic Photochemistry (Ed.: A. Padwa), Dekker, New York, 1981, vol. 5, pp. 1-123.
17. [9a] Enol ethers: S. H. Schroeter, C. M. Orlando Jr., J. Org. Chem. 1969, 34, 1181-1187.
18. H.-S. Ryang, K. Shima, H. Sakurai, J. Org. Chem. 1973, 38, 2860-2865.
19. J. Mattay, J. Gersdorf, U. Freudenberg, Tetrahedron Lett. 1984, 25, 817-820.
20. H. A. J. Carless, G. K. Fekarurhobo, Tetrahedron Lett. 1985, 26, 4407-4410 and references cited therein.
21. [9b] Diketene: T. Kato, M. Sato, Y. Kitagawa, Chem. Pharm. Bull. 1975, 23, 365-370.
22. [9c] Dihydrofurans: H. A. J. Carless, D. J. Haywood, J. Chem. Soc., Chem. Commun. 1980, 1067-1068.
23. A. G. Griesbeck, S. Stadtmüller, Chem. Ber. 1990, 123, 357-362.
24. A. G. Griesbeck, S. Stadtmüller, J. Am. Chem. Soc. 1991, 113, 6923-6928.
25. [9d] Enol acetates: Y. Araki, J.-I. Nagasawa, Y. Ishido, J. Chem. Soc., Perkin Trans. 1, 1981, 12-23.
26. H. Ruotsalainen, T. Kärki, Acta Chem. Scand., Ser. B 1983, B37, 151-154.
27. S. Vasudevan, C. P. Brock, D. S. Watt, H. Morita, J. Org. Chem. 1994, 59, 4677-4679.
28. [9e] Enediol equivalents: H.-D. Scharf, J. Mattay, Tetrahedron Lett. 1976, 3509-3512.
29. H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath, J. Runsink, J. Am. Chem. Soc. 1989, 111, 5367-5373.
30. Regioselective synthesis of 3-methylthiooxetanes: N. Khan, T. H. Morris, E. H. Smith, R. Walsh, J. Chem. Soc., Perkin Trans. 1991, 865-870.
31. Reviews: [11a] J. K. Rasmussen, Synthesis 1977, 91-103.
32. [11b] P. Brownbridge, Synthesis 1983, 1-28.
33. [12a] Y. Araki, J. I. Nagasawa, Y. Ishido, Carbohydr. Res. 1981, 91, 77-84.
34. [12b] N. Shimizu, S. Yamaoka, Y. Tsuno, Bull. Chem. Soc. Jpn. 1983, 56, 3853-3854.
35. [13a] T. Bach, Tetrahedron Lett. 1991, 32, 7037-7038.
36. [13b] T. Bach, K. Jödicke, Chem. Ber. 1993, 126, 2457-2466.
37. First detection of the preoxetane triplet 1,4-biradical: [14a] S. C. Freilich, K. S. Peters, J. Am. Chem. Soc. 1981, 103, 6255-6257.
38. [14b] S. C. Freilich, K. S. Peters, J. Am. Chem. Soc. 1985, 107, 3819-3822.
39. Review: A. G. Griesbeck, H. Mauder, S. Stadtmüller, Acc. Chem. Res. 1994, 27, 70-75.
40. T. Bach, Liebigs Ann. 1995, 855-866.
41. T. Bach, K. Kather, J. Prakt. Chem. 1996, 338, 750-753.
42. [18a] N. J. Turro, P. A. Wriede, J. Am. Chem. Soc. 1970, 92, 320-329.
43. [18b] N. C. Yang, M. Kimura, W. Eisenhardt, J. Am. Chem. Soc. 1973, 95, 5058-5060. - See also:
44. [18c] G. Jones II, M. Santhanam, S.-H. Chiang, J. Am. Chem. Soc. 1980, 102, 6088-6095.
45. T. Bach, Tetrahedron Lett. 1994, 35, 5845-5848.
46. Reviews on the facial diastereoselectivity in Paternò-Büchi reactions: [20a] H. Buschmann, H.-D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480-518;
47. Angew. Chem. Int. Ed. Engl. 1991, 30, 477-515.
48. [20b] Y. Inoue, Chem. Rev. 1992, 92, 741-770.
49. Review: R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
50. [2a] T. Bach, K. Jödicke, K. Kather, J. Hecht, Angew. Chem. 1995, 107, 2455-2457;
51. Angew. Chem. Int. Ed. Engl. 1995, 34, 2271-2273.
52. [22b] T. Bach, K. Jödicke, K. Kather, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 2437-2445.
53. T. Bach, K. Jödicke, B. Wibbeling, Tetrahedron 1996, 52, 10861-10878.
54. M. Kawanisi, K. Kamogawa, T. Okada, H. Nozaki, Tetrahedron 1968, 24, 6557-6562.
55. [25a] D. Döpp, H. R. Memarian, M. A. Fischer, A. M. J. van Eijk, C. A. G. O. Varma, Chem. Ber. 1992, 125, 983-984.
56. [25b] D. Döpp, M.-A. Fischer, Recl. Trav. Chim. Pays-Bas 1995, 114, 498-503.
57. For a previous report on the photocycloaddition of benzophenone and N-vinylpyrrolidone: M. Ogata, H. Matsumoto, H. Kano, Kogyo Kagatu Zashi 1969, 72, 105-199.
58. [27a] H. Breederveld, Recl. Trav. Chim. Pays-Bas 1960, 79, 401-407.
59. [27b] O. Meth-Cohn, K. T. Westwood, J. Chem. Soc., Perkin Trans. 1 1984, 1173-1182.
60. T. Bach, Angew. Chem. 1996, 108, 976-977;
61. Angew. Chem. Int. Ed. Engl. 1996, 35, 884-886.
62. T. Bach, J. Schröder, manuscript in preparation.
63. T. Bach, J. Schröder, Universität Marburg, unpublished results.
64. T. Bach, presented at the 2nd Joint Meeting of the French, German and Swiss Sections of the EPA, Book of Abstracts, Konstanz, 1996, p. 27.
65. [10][13b][27].
66. T. Bach, K. Rather, Tetrahedron 1994, 50, 12319-12328.
67. K. Kather, Ph. D. Dissertation, Universität Münster, 1996.
68. Selected references for previous work on the intramolecular nucleophilic substitution of oxetanes: [35a] M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1984, 25, 4549-4552.
69. [35b] A. Itoh, Y. Hirose, H. Kashiwagi, Y. Masaki, Heterocycles 1994, 38, 2165-2169.
70. T. Bach, K. Kather, J. Org. Chem. 1996, 61, 7642-7643.
71. T. Bach, K. Kather, J. Org. Chem. 1996, 61, 3900-3901.
72. J. S. Sawyer, A. Kucerovy, T. L. Macdonald, G. J. McGarvey, J. Am. Chem. Soc. 1988, 110, 842-853.
73. Y. Kitagawa, A. Itoh, S. Hashimoto, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 3864-3867.
74. D. R. Morton, R. A. Morge, J. Org. Chem. 1978, 43, 2093-2101.
75. [41a] T. Bach, Tetrahedron Lett. 1994, 35, 1855-1858.
76. [41b] T. Bach, Liebigs Ann. 1995, 1045-1053.
77. T. Bach, C. Lange, Tetrahedron Lett. 1996, 37, 4363-4364.
78. T. Bach, F. Eilers, K. Kather, Liebigs Ann. 1997, in press.
79. T. Bach, J. Schröder, Tetrahedron Lett. 1997, 38, in press.