Direct transformation of silyl enol ethers into functionalized allenes

Chemistry - A European Journal

Volumn 7, Issue 3, 2001, Pages 573-584

  Langer, Peter ^a   Döring, Manfred ^b   Seyferth, Dietmar ^c   Görls, Helmar ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Allenes; Domino reactions; Ketenimines; Lithium; Silyl enol ethers

Indexed keywords

1,1 BIS(HYDROXYMETHYL)ALLENE DERIVATIVE; 1,1 DILITHIO 3,3 DIPHENYLALLENE; ALCOHOL; ALLENE DERIVATIVE; CHLORINE DERIVATIVE; DIMETHYL SULFATE; ETHER DERIVATIVE; IMINE; KETENE DERIVATIVE; KETONE; LITHIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0035793250     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010202)7:3<573::AID-CHEM573>3.0.CO;2-I     Document Type: Article

References (89)

1. a) For reviews on the synthesis and reactions of allenes, see: H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley, New York, 1984;
2. b) R. H. Schlessinger, C. P. Bergstrom, J. Org. Chem. 1995, 60, 16, and references therein;
3. for transition metal catalyzed reactions of allenes, see: c) M. Ahmar, B. Cazes, J. Goré, Tetrahedron 1987, 43, 3453;
4. d) B. Friess, B. Cazes, J. Goré, Tetrahedron Lett. 1988, 43, 4089;
5. e) S. Ma, E.-I. Negishi, J. Am. Chem. Soc. 1995, 117, 6345;
6. f) R. C. Larock, N. G. Berrios-Pena, C. A. Fried, J. Org. Chem. 1991, 56, 2615;
7. g) D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Am. Chem. Soc. 1991, 113, 2652;
8. h) R. D. Walkup, L. Guan, M. D. Mosher, S. W. Kim, Y. S. Kim, Synlett 1993, 88;
9. i) M. E. Piotti, H. Alper, J. Org. Chem. 1994, 59, 1956;
10. j) A. S. K. Hashmi, T. L. Ruppert, T. Knöfel, J. W. Bats, J. Org. Chem. 1997, 62, 7295;
11. k) R. Grigg, V. Loganathan, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron 1996, 52, 11479;
12. l) T. Doi, A. Yanagisawa, K. Nakanishi, K. Yamamoto, T. Takahashi, J. Org. Chem. 1996, 61, 2602;
13. m) B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837;
14. Angew. Chem. Int. Ed. Engl. 1997, 36, 1750.
15. For the base-mediated transformation of enol phosphates into alkynes, see: a) E.-I. Negishi, A. O. King, W. L. Klima, J. Org. Chem. 1980, 45, 2526;
16. for allenes, see: b) K. M. Brummond, E. A. Dingess, J. L. Kent, J. Org. Chem. 1996, 61, 6096;
17. for the use of vinyl halides and enol triflates, see: c) F. Naso, L. Ronzini, J. Chem. Soc. Perkin Trans 1 1974, 340;
18. d) P. J. Stang, R. J. Hargrove, J. Org. Chem. 1975, 40, 657.
19. a) M. T. Reetz, Angew. Chem. 1982, 94, 97;
20. Angew. Chem. Int. Ed. Engl. 1982, 21, 96;
21. b) P. Brownbridge, Synthesis 1983, 1, 85;
22. c) T. Mukaiyama, Angew. Chem. 1977, 89, 858;
23. Angew. Chem. Int. Ed. Engl. 1977, 16, 817;
24. d) I. Ryu, S. Murai, I. Niwa, N. Sonoda, Synthesis 1977, 874.
25. a) E. Baciocchi, A. Casu, R. Ruzziconi, Tetrahedron Lett. 1989, 3707;
26. b) A. B. Paolobelli, D. Latini, R. Ruzziconi, Tetrahedron Lett. 1993, 721;
27. c) P. Langer, V. Köhler, Chem. Commun. 2000, ■page number■.
28. For a preliminary communication, see: a) D. Seyferth, P. Langer, M. Döring, Organometallics 1998, 14, 4457;
29. b) P. Langer, Chem. Commun. 1999, 1217;
30. see also: c) P. Langer, M. Döring, D. Seyferth, Chem. Commun. 1998, 1927;
31. see also: d) O. Witt, H. Mauser, T. Friedl, D. Wilhelm, T. Clark, J. Org. Chem. 1998, 65, 959;
32. e) D. Seyferth, T. Wang, P. Langer, R. L. Ostrander, A. L. Rheingold, Organometallics 1997, 16, 2413.
33. J. K. Rasmussen, A. Hassner, J. Org. Chem. 1974, 39, 2558.
34. A related rearrangement has been previously reported by Corey et al. who obtained α-triisopropylsilyl ketones from carbanions of triisopropylsilyl enol ethers of 4-tert-butylcyclohexanone derivatives: E. J. Corey, C. Rücker, Tetrahedron Lett. 1984, 25, 4345.
35. a) G. Stork, P. Hudrlik, J. Am. Chem. Soc. 1968, 90, 4462, see also Ref. [7];
36. nd Ed., Wiley, 1991, p. 68-87.
37. R. B. Bates, I. M. Kroposki, D. E. Potter, J. Org. Chem. 1972, 37, 560.
38. 2t(Bu) which were formed by silylation of intermediates C or D, respectively.
39. Aldehydes and ketones have been converted into terminal allenes by reaction with α-lithiovinylsilanes and subsequent fluoride-mediated Peterson olefination of the 1-hydroxy-2-trimethylsilylpropenes formed: T. H. Chan, W. Mychajlowskij, B. S. Ong, D. N. Harpp, J. Org. Chem. 1978, 43, 1526.
40. For the formation of polylithioallenes, see: a) F. Jaffe, J. Organomet. Chem. 1970, 23, 53;
41. b) W. Priester, R. West, T. L. Chwang, J. Am. Chem. Soc. 1976, 8413;
42. c) W. Priester, R. West, J. Am. Chem. Soc. 1976, 8421.
43. P. Binger, P. Müller, R. Wenz, R. Mynott, Angew. Chem. 1990, 102, 1070;
44. Angew. Chem. Int. Ed. Engl. 1990, 29, 1037: (Chemical Equation Presented)
45. L. Skattebøl, Acta Chem. Scand. 1963, 17, 1683.
46. a) 1,1-Diphenyl-3,3-dimethylallene: G. Wittig, A. Haag, Chem. Ber. 1963, 96, 1535;
47. b) 6 f: E. Grovenstein, K.-W. Chiu, B. B. Patil, J. Am. Chem. Soc. 1980, 102, 5848.
48. For the application of the HSAB concept on the chemistry of lithiated allenes, see ref. [15b]. For studies on the structure of allenyl-propargyllithium reagents in solution, see: H. J. Reich, J. E. Holladay, Angew. Chem. 1996, 108, 2498;
49. Angew. Chem. Int. Ed. Engl. 1996, 55, 2365, and literature cited thererein.
50. A 1,1-di(hydroxymethyl)allene has been previously prepared by a different route in 17% yield: H. Mori, K. Ikoma, S. Katsumura, Chem. Commun. 1997, 2243.
51. S. Hagen, M. S. Bratcher, M. S. Erickson, G. Zimmermann, L. T. Scott, Angew. Chem. 1997, 109, 407;
52. Angew. Chem. Int. Ed. Engl. 1997, 36, 406.
53. a) F. Toda, N. Ooi, K. Akagi, Bull. Chem. Soc. Jpn. 1971, 44, 1050;
54. b) N. J. Head, G. A. Olah, G. K. S. Prakash, J. Am. Chem. Soc. 1995, 117, 11205.
55. For reviews of domino reactions, see: a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137;
56. Angew. Chem. Int. Ed. Engl. 1993, 32, 131;
57. b) A. deMeijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473;
58. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
59. a) H. Hopf, G. Maas, Angew. Chem. 1992, 104, 953;
60. Angew. Chem. Int. Ed. Engl. 1992, 31, 931;
61. b) F. Toda, K. Tanaka, I. Sano, T. Isozaki, Angew. Chem. 1994, 106, 1856;
62. Angew. Chem. Int. Ed. Engl. 1994, 33, 1757;
63. c) H. Hopf, P. G. Jones, P. Bubenitschek, C. Werner, Angew. Chem. 1995, 107, 2592;
64. Angew. Chem. Int. Ed. Engl. 1995, 34, 2367.
65. a) S. Blechert, R. Knier, H. Schroers, T. Wirth, Synthesis 1995, 592;
66. b) R. Grigg, V. Loganathan, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron 1996, 52, 11479;
67. c) M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. 1996, 108, 1952;
68. Angew. Chem. Int. Ed. Engl. 1996, 35, 1843.
69. F. W. Nader, C.-D. Wacker, Angew. Chem. 1985, 97, 876;
70. Angew. Chem. Int. Ed. Engl. 1985, 24, 851.
71. For the failure of a palladium-catalyzed synthesis of a 5,5,6-pentafulvene, see: G. Dyker, F. Nerenz, P. Siemsen, P. Bubenitschek, P. G. Jones, Chem. Ber. 1996, 129, 1265.
72. M. Hoang, T. Gadosy, H. Ghazi, D.-F. Hou, A. C. Hopkinson, L. J. Johnston, E. Lee-Ruff, J. Org. Chem. 1998, 63, 7168.
73. J. Klein, J. Y. Backer, J. Chem. Soc. Chem. Commun. 1973, 576.
74. 1NMR and IR data and the melting point (194-196°C) of 13c were identical to those of cis-1,2-diphenyl-anti-3,4-dibenzylidenecyclobutane which was prepared by heating 1,3-diphenylallene in refluxing benzene: E. V. Dehmlow, Chem. Ber. 1967, 100, 3260.
75. A mixture of 13d and 13c has been previously prepared by a different route; however, the isomers were not separated: E. V. Dehmlow, G. C. Ezimora, Tetrahedron Lett. 1971, 1599.
76. J. F. Wolfe, T. P. Murray, J. Org. Chem. 1971, 36, 354.
77. J. Klein, S. Brenner, Tetrahedron 1970, 2345.
78. B. L. Groh, G. R. Magrum, T. J. Barton, J. Am. Chem. Soc. 1987, 109, 7568.
79. T. Shimizu, F. Hojo, W. Ando, J. Am. Chem. Soc. 1993, 115, 3111.
80. a) R. L. Danheiser, D. J. Carini, J. Org. Chem. 1980, 45, 3925;
81. b) R. L. Danheiser, D. J. Carini, A. J. Basak, J. Am. Chem. Soc. 1981, 103, 1604;
82. c) M. Montury, B. Psaume, J. Goré, Tetrahedron Lett. 1980, 163;
83. d) A. Jellal, M. Santelli, Tetrahedron Lett. 1980, 4487.
84. a) J. A. Marshall, X. J. Wang, J. Org. Chem. 1992, 57, 1242;
85. b) J. Haruta, K. Nishi, S. Matsuda, S. Akai, Y. Tamura, Y. Kita, J. Org. Chem. 1990, 55, 4853.
86. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-145872 (8g), CCDC-140090 (9a), and CCDC-145595 (10b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223336-033; e-mail: depsoti@ccdc.cam.ac.uk)..
87. MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
88. G. M. Sheldrick, Acta Crystaltogr. Sect. A 1990, 46, 467.
89. G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1993.