Stereoselective construction of the Tetrahydrofuran nucleus by alkoxyl radical cyclizations

European Journal of Organic Chemistry

Volumn , Issue 4, 2001, Pages 619-632

  Hartung, Jens ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Asymmetric synthesis; Cyclizations; Heterocycles; Oxygen; Radicals

Indexed keywords

ALKALOID; HETEROCYCLIC COMPOUND; MUSCARINE; OXYGEN; RADICAL; TETRAHYDROFURAN;

CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035131973     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200102)2001:4<619::AID-EJOC619>3.0.CO;2-A     Document Type: Short Survey

References (125)

1. [1a] M. Gomberg, Chem. Ber. 1900, 33, 3150-3163.
2. [1b] M. Gomberg, J. Am. Chem. Soc. 1900, 22, 757-771.
3. [2a] C. Walling, Free Radicals in Solution, Wiley, New York, 1957.
4. [2b] M. Julia, Acc. Chem. Res. 1971, 4, 386-392.
5. [2c] J. Kochi, Free Radicals, Wiley, New York, 1973.
6. [2d] F. Minisci, Acc. Chem. Res. 1975, 8, 165-171.
7. [2e] J. Tedder, Angew. Chem. 1982, 94, 433-442;
8. Angew. Chem. Int. Ed. Engl. 1982, 21, 401-410.
9. [2f] C. Rüchardt, Top. Curr. Chem. 1980, 88, 1-32.
10. [2g] G. A. Russel, Acc. Chem. Res. 1989, 22, 1-8.
11. C-Radikale, in Houben-Weyl - Methoden der Organischen Chemie (Eds.: M. Regitz, B. Giese), 4th edition, Vol E19a, part 1, Thieme Verlag Stuttgart, 1989.
12. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986.
13. B. Giese, N. Porter, D. P. Curran, Stereochemistry of Radical Reactions, VCH, Weinheim, 1995.
14. J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995.
15. D. H. R. Barton, S. I. Parekh, Half a Century of Free Radical Chemistry, Cambridge University Press, Cambridge, 1993.
16. [8a] D. Crich, L. Quintero, Chem. Rev. 1989, 89, 1413-1432.
17. [8b] A. L. J. Beckwith, J. Chem. Soc., Rev.1993, 22, 143-151.
18. [8c] M. Ramaiah, Tetrahedron 1987, 43, 3541-3676.
19. [9a] P. Renaud, M. Gerster, Angew. Chem. 1998, 110, 2704-2722;
20. Angew. Chem. Int. Ed. 1998, 110, 2562-2579.
21. [9b] N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 296-304.
22. [9c] J. L. Esker, M. Newcomb, Adv. Heterocycl. Chem. 1993, 58, 1-45.
23. D. H. R. Barton, J. M. Beaton, L. E. Geller, M. M. Pechet, J. Am. Chem. Soc. 1960, 82, 2640-2641.
24. [11a] J. Kalvoda, K. Heusler, Synthesis 1971, 501-526.
25. [11b] G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095-7129.
26. [12a] P. Dowd, W. Zhang, Chem. Rev. 1993, 93, 2091-2115.
27. [12b] A. Nishida, Y. -I. Kakimoto, Y. Ogasawara, N. Kawahara, M. Nishida, H. Takayanasi, Tetrahedron Lett. 1997, 38, 5519-5522.
28. [12c] A. L. J. Beckwith, B. P. Hay, J. Am. Chem. Soc. 1989, 111, 230-234.
29. G. M. Keserú, M. Nógrádi, Stud. Nat. Prod. Chem. 1998, 20, 263-322.
30. [14a] V. Ullrich, R. Brugger, Angew. Chem. 1994, 106, 1987-1996;
31. Angew. Chem. Int. Ed. Engl. 1994, 33, 1911-1919.
32. [14b] W. Adam, J. Cadet, F. Dall'Aqua, B. Epe, D. Ramaiah, C. R. Saha-Möller, Angew. Chem. 1995, 107, 91-93;
33. Angew. Chem. Int. Ed. Engl. 1995, 34, 107-110.
34. J. A. Howard, J. C. Scaiano, Kinetische Daten von Radikalreaktionen in Lösung - Oxyl, Peroxyl und verwandte Radikale in Landolt-Börnstein, Zahlenwerte und Funktionen aus Naturwissenschaft und Technik, New Series, Vol. 13, Part D, Springer, Berlin, 1984.
35. A. L. J. Beckwith, B. P. Hay, J. Am. Chem. Soc. 1988, 110, 4415-4416.
36. A. L. J. Beckwith, B. P. Hay, G. M. Williams, J. Chem. Soc., Chem. Commun. 1989, 1202-1203.
37. J. Hartung, F. Gallou, J. Org. Chem. 1995, 60, 6706-6716.
38. J. Hartung, M. Hiller, P. Schmidt, Liebigs Ann. 1996, 1425-1436.
39. J. Hartung, M. Hiller, P. Schmidt, Chem. Eur. J. 1996, 2, 1014-1023.
40. J. Hartung, M. Schwarz, I. Svoboda, H. Fueß, M.-T. Duarte, Eur. J. Org. Chem. 1999, 1275-1290.
41. J. Hartung, R. Kneuer, Eur. J. Org. Chem. 2000, 1677-1683.
42. [23a] R. J. Elliot, W. G. Richards, J. Chem. Soc., Perkin Trans. 2 1982, 943-945.
43. [23b] M. J. Jones, G. Moad, E. Rizzardo, D. H. Solomon, J. Org. Chem. 1989, 54, 1607-1611.
44. R. D. Bach, P. Y. Ayala, H. B. Schlegel, J. Am. Chem. Soc. 1996, 118, 12758-12765.
45. D. H. R. Barton, J. M. Beaton, L. E. Geller, M. M. Pechet, J. Am. Chem. Soc. 1961, 83, 4076-4083.
46. [26a] M. J. Begley, R. J. Fletcher, J. A. Murphy, M. S. Sherburn, J. Chem. Soc., Chem. Commun. 1993, 1723-1725.
47. [26b] C. G. Francisco, E. I. León, P. Moreno, E. Suárez, Tetrahedron: Asymmetry 1998, 9, 2975-2978.
48. D. J. Pasto, F. Cottard, Tetrahedron Lett. 1994, 35, 4303-4306.
49. [28a] C. Walling, Bull. Soc. Chim. Fr. 1968, 1609-1615.
50. [28b] C. Walling, R. T. Clark, J. Am. Chem. Soc. 1974, 96, 4530-4534.
51. H. J. Reich, S. Wollowitz, J. Am. Chem. Soc. 1982, 104, 7051-7059.
52. R. Kneuer, Diploma Thesis, Universität Würzburg, 1996.
53. J. Hartung, R. Kneuer, M. Schwarz, I. Svoboda, H. Fueß, Eur. J. Org. Chem. 1999, 97-106.
54. A. L. J. Beckwith, B. P. Hay, J. Org. Chem. 1989, 54, 4330-4334.
55. D. H. R. Barton, P. Blundell, J. C. Jaszberenyi, Tetrahedron Lett. 1989, 30, 2341-2344.
56. S. Kim, T. A. Lee, Synlett 1997, 950-952.
57. S. Kim, T. A. Lee, Y. Song, Synlett 1998, 471-472.
58. [36a] J. E. Leffler, An Introduction to Free Radicals, Wiley, New York, 1993, 126-147.
59. [36b] R. A. Sheldon, Synthesis and uses of Alkylhydroperoxides and Dialkylperoxides, in The Chemistry of Functional Groups (Ed.: S. Patai), Vol. 33, Wiley, Chichester, 1993, 161-200. -
60. K. U. Ingold, Acc. Chem. Res. 1969, 2, 1-9.
61. [37a] J. Hartung, B. Giese, Chem. Ber. 1991, 124, 387-390.
62. [37b] M. Kijima, H. Yamashita, M. Kainosho, T. Sato, J. Org. Chem. 1994, 59, 6748-6752.
63. [37c] B. D. Gupta, M. Roy, I. Das, J. Organometal. Chem. 1990, 397, 219-230.
64. F. A. Chavez, J. A. Briones, M. M. Olmstead, P. K. Mascharak, Inorg. Chem. 1999, 38, 1603-1608.
65. [39a] J.-M. Surzur, M.-P. Bertrand, Bull. Soc. Chim. Fr. 1973, 1861-1867.
66. [39b] V. M. Micovic, R. I. Mamuzic, D. Jeremic, M. Lj. Mihailovic, Tetrahedron 1964, 20, 2279-2287.
67. A. Clerici, F. Minisci, K. Ogawa, J.-M. Surzur, Tetrahedron Lett. 1978, 1149-1152.
68. T.-L. Ho, Cerium(IV) Oxidations of Organic Compounds in Organic Synthesis by Oxidation with Metal Compounds (Eds.: W. J. Mijs, C. R. H. I. De Jonge), Plenum Press, New York, 1986, 569-631.
69. [42a] J. L. Courtneidge, J. Lusztyk, D. Pagé, Tetrahedron Lett. 1994, 35, 1003-1006.
70. [42b] A. Boto, C. Betancor, T. Prangé, E. Suárez, J. Org. Chem. 1994, 59, 4393-4401.
71. [43a] D. H. R. Barton, R. S. H. Motherwell, W. B. Motherwell, J. Chem. Soc., Perkin. Trans. 1 1981, 2363-2367.
72. [43b] D. J. Pasto, F. Cottard, C. Picconatto, J. Org. Chem. 1994, 59, 7172-7177.
73. [43c] A. G. Davies, B. Muggleton, J. A. A. Havari, M.-W. Tse, J. Chem. Soc., Perkin Trans. 2 1981, 1132-1137.
74. J. C. Walton, P. A. Baguley, Angew. Chem. 1998, 110, 3272-3283;
75. Angew. Chem. Int. Ed. Engl. 1998, 110, 3072-3082.
76. For reviews on thiocarbonyl compounds see: [45a] W. Walter, E. Schaumann, Synthesis 1971, 111-130.
77. [45b] P. Metzner, Top. Curr. Chem. 1999, 204, 127-181.
78. J. Hartung, I. Svoboda, H. Fuess, Acta Cryst. 1996, C52, 2841-2844.
79. J. Hartung, I. Svoboda, H. Fuess, Z. Kristallogr. 1998, 213, 319-320
80. [48a] D. H. R. Barton, M. Samadi, Tetrahedron 1992, 48, 7083-7090.
81. [48b] D. H. R. Barton, C. Chen, G. M. Wall, Tetrahedron 1991, 47, 6127-6138.
82. J. Hartung, Synlett 1996, 1206-1209.
83. J. Hartung, M. Hiller, M. Schwarz, I. Svoboda, H. Fuess, Liebigs Ann. 1996, 2091-2097.
84. W. Walter, K.-P. Rueß, Liebigs Ann. Chem. 1971, 743, 167-176.
85. [31]. - Crystal structure analysis of N-hydroxypyridine-4(1H)-thione: J. Hartung, I. Svoboda, H. Fuess, M. -T. Duarte, Acta Cryst. 1997, C53, 1631-1634.
86. D. H. R. Barton, D. Crich, G. Kretzschmar, J. Chem. Soc., Perkin Trans. 1 1986, 39-53.
87. [54a] J. Hartung, M. Schwarz, Synlett 1997, 848-850.
88. [54b] J. Hartung, M. Schwarz, Synlett 1997, 1116.
89. J. Hartung, M. Schwarz, Org. Synth., accepted.
90. [21] and its structure as a heterocyclic N-oxide were reconfirmed in these independent control experiments.
91. J.-M. Surzur, M.-P. Bertrand, R. Nougier, Tetrahedron Lett. 1969, 4197-4200.
92. R. D. Rieke, N. A. Moore, J. Org. Chem. 1972, 37, 413-418.
93. A. L. J. Beckwith, K. U. Ingold, in Rearrangements in Ground and Excited States (Ed.: P. de Mayo), Vol. 1, 203-205, Academic Press, New York, 1980.
94. B. C. Gilbert, R. G. G. Holmes, H. A. H. Laue, R. O. C. Normann, J. Chem. Soc., Perkin Trans. 2 1976, 1047-1052.
95. A. Johns, J. A. Murphy, Tetrahedron Lett. 1988, 29, 837-840.
96. [62a] B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K. J. Kulicke, F. Trach, Org. React. 1996, 48, 301-856.
97. [62b] A. Martinez-Grau, J. Marco-Contelles, Chem. Soc. Rev. 1998, 27, 155-172.
98. [63a] D. P. Curran, Synthesis 1988, 417-439.
99. [63b] D. P. Curran, Synthesis 1988, 489-513.
100. G. Pattenden, Chem. Soc. Rev. 1988, 17, 361-382.
101. [65a] T. V. RajanBabu, Acc. Chem. Res. 1991, 24, 139-145.
102. [65b] T. V. RajanBabu, T. Fukunaga, G. S. Reddy, J. Am. Chem. Soc. 1989, 111, 1759-1769.
103. A. L. J. Beckwith, C. H. Schiesser, Tetrahedron 1985, 41, 3925-3941.
104. D. Griller, K. U. Ingold, Acc. Chem. Res. 1980, 13, 317-323.
105. [68a] P. Schmid, D. Griller, K. U. Ingold, Int. J. Chem. Kinet 1979, 11, 333-338.
106. [68b] D. Lal, D. Griller, S. Husband, K. U. Ingold, J. Am. Chem. Soc. 1974, 96, 6355-6358.
107. P. A. Bartlett, Asymmetric Synthesis 1984, 3, 411-453.
108. J.-C. Harmange, B. Ficadère, Tetrahedron: Asymmetry 1993, 4, 1711-1754.
109. C. K. Hanckock, E. A. Meyers, B. J. Yager, J. Am. Chem. Soc. 1961, 83, 4211-4213.
110. D. A. Avila, J. Lusztyk, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 6576-6577.
111. J. Hartung, Habilitation Thesis, Universität Würzburg, 1998.
112. J. M. Tanko, N. K. Suleman, in Energetics of Organic Free Radicals (Eds.: J. A. M. Simões, A. Greenberg, J. F. Liebman), Chapmann & Hall, 1996, pp 225-293.
113. W. Damm, B. Giese, J. Hartung, T. Hasskerl, K. N. Houk, O. Hüter, H. Zipse, J. Am. Chem. Soc. 1992, 114, 4067-4079.
114. D. C. Spellmeyer, K. N. Houk, J. Org. Chem. 1987, 52, 959-974.
115. [77a] M. W. Wong, A. Pross, L. Radom, J. Am. Chem. Soc. 1994, 116, 11938-11943.
116. [77b] M. W. Wong, L. Radom, J. Phys. Chem. 1995, 99, 8582-8588.
117. J. Hartung, R. Stowasser, D. Vitt, G. Bringmann, Angew. Chem. 1996, 108, 3056-3059;
118. Angew. Chem. Int. Ed. Engl. 1996, 35, 2820-2823.
119. C. H. Eugster, Naturwissenschaften 1968, 55, 305-313.
120. P.-C. Wang, M. M. Joullié, The Alkaloids 1984, 23, 327-380.
121. A. M. Mubarak, D. M. Brown, J. Chem. Soc., Perkin Trans. 1 1982, 809-813.
122. S. Pochet, T. Huynh-Dinh, J. Org. Chem. 1982, 47, 193-198.
123. S. J. Lippard, J. M. Berg, Bioanorganische Chemie, Spektrum-Verlag, Heidelberg 1995.
124. [84a] J. Stubbe, W. A. v. der Donk, Chem. Rev. 1998, 98, 705-762.
125. [84b] R. Schnepf, A. Sokolowski, J. Müller, V. Bachler, K. Wieghardt, P. Hildebrandt, J. Am. Chem. Soc. 1998, 120, 2352-2364.