Cyclic Diynes by Alkyne Metathesis

Synthesis

Volumn , Issue 16, 2003, Pages 2535-2541

  Hellbach, Björn ^a   Gleiter, Rolf ^a   Rominger, Frank ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkyne metathesis; Cyclic diynes; Cyclizations; Macrocycles; Molybdenum

Indexed keywords

MOLECULAR STRUCTURE; MOLYBDENUM COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

RING CLOSING METATHESIS;

OLEFINS;

ALKYNE DERIVATIVE; CARBENE; CYCLODOCOSA 1,12 DIYNE; CYCLOEICOSA 1,11 DIYNE; CYCLOHEXACOSA 1,14 DIYNE; CYCLOHEXADECA 1,9 DIYNE; CYCLOOCTADECA 1,10 DIYNE; CYCLOTETRACOSA 1,13 DIYNE; CYCLOTETRADECYNE; DODECA 2,10 DIYNE; HEPTADECA 2,15 DIYNE; HEXADECA 2,14 DIYNE; METHYL GROUP; MOLYBDENUM COMPLEX; OCTADECA 2,16 DIYNE; PENTADECA 2,13 DIYNE; TETRADECA 2,12 DIYNE; TRIDECA 2,11 DIYNE; UNCLASSIFIED DRUG; UNDECA 2,9 DIYNE;

ARTICLE; CHEMICAL PARAMETERS; METHODOLOGY; RING CLOSING METATHESIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0344442246     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42421     Document Type: Article

References (49)

1. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
2. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
3. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
4. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
5. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
6. Reviews see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037; Angew. Chem. 1997, 109, 2124. (b) Armstrong, S. K. J. Chem. Soc, Perkin Trans. 1 1998, 371. (c) Grubbs, R. H.; Cheng, S. Tetrahedron 1998, 54, 4413. (d) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012; Angew. Chem. 2000, 122, 3140.
7. Wittig, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.
8. McMurry, J. E. Chem. Rev. 1989, 89, 1513.
9. 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al., cf.: (a) Mortreux, A.; Blanchard, M. J. Chem. Soc., Chem. Commun. 1974, 786. (b) Mortreux, A.; Dy, N.; Blanchard, M. J. Mol. Catal. 1975, 1, 101. (c) Mortreux, A.; Delgrange, J. C.; Blanchard, M.; Lubochinsky, B. J. Mol. Catal. 1977, 2, 73. (d) For comments on the reactive intermediates formed under these conditions see: McCullough, L. G.; Schrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
10. 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al., cf.: (a) Mortreux, A.; Blanchard, M. J. Chem. Soc., Chem. Commun. 1974, 786. (b) Mortreux, A.; Dy, N.; Blanchard, M. J. Mol. Catal. 1975, 1, 101. (c) Mortreux, A.; Delgrange, J. C.; Blanchard, M.; Lubochinsky, B. J. Mol. Catal. 1977, 2, 73. (d) For comments on the reactive intermediates formed under these conditions see: McCullough, L. G.; Schrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
11. 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al., cf.: (a) Mortreux, A.; Blanchard, M. J. Chem. Soc., Chem. Commun. 1974, 786. (b) Mortreux, A.; Dy, N.; Blanchard, M. J. Mol. Catal. 1975, 1, 101. (c) Mortreux, A.; Delgrange, J. C.; Blanchard, M.; Lubochinsky, B. J. Mol. Catal. 1977, 2, 73. (d) For comments on the reactive intermediates formed under these conditions see: McCullough, L. G.; Schrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
12. 6 and phenol additives has been originally proposed as alkyne metathesis catalyst by Mortreux et al., cf.: (a) Mortreux, A.; Blanchard, M. J. Chem. Soc., Chem. Commun. 1974, 786. (b) Mortreux, A.; Dy, N.; Blanchard, M. J. Mol. Catal. 1975, 1, 101. (c) Mortreux, A.; Delgrange, J. C.; Blanchard, M.; Lubochinsky, B. J. Mol. Catal. 1977, 2, 73. (d) For comments on the reactive intermediates formed under these conditions see: McCullough, L. G.; Schrock, R. R. J. Am. Chem. Soc. 1984, 106, 4067.
13. Katz, T. J.; McGinnis, J. J. Am. Chem. Soc. 1975, 97, 1592.
14. For applications of the Mortreux system see: (a) Villemin, D.; Cadiot, P. Tetrahedron Lett. 1982, 23, 5139. (b) Du Plessis, J. A. K.; Vosloo, H. C. M. J. Mol. Catal. 1991, 65, 51. (c) Kaneta, N.; Hirai, T.; Mori, M. Chem. Lett. 1995, 627. (d) Kaneta, N.; Hikichi, K.; Asaka, S.-I.; Uemura, M.; Mori, M. Chem. Lett. 1995, 1055.
15. For applications of the Mortreux system see: (a) Villemin, D.; Cadiot, P. Tetrahedron Lett. 1982, 23, 5139. (b) Du Plessis, J. A. K.; Vosloo, H. C. M. J. Mol. Catal. 1991, 65, 51. (c) Kaneta, N.; Hirai, T.; Mori, M. Chem. Lett. 1995, 627. (d) Kaneta, N.; Hikichi, K.; Asaka, S.-I.; Uemura, M.; Mori, M. Chem. Lett. 1995, 1055.
16. For applications of the Mortreux system see: (a) Villemin, D.; Cadiot, P. Tetrahedron Lett. 1982, 23, 5139. (b) Du Plessis, J. A. K.; Vosloo, H. C. M. J. Mol. Catal. 1991, 65, 51. (c) Kaneta, N.; Hirai, T.; Mori, M. Chem. Lett. 1995, 627. (d) Kaneta, N.; Hikichi, K.; Asaka, S.-I.; Uemura, M.; Mori, M. Chem. Lett. 1995, 1055.
17. For applications of the Mortreux system see: (a) Villemin, D.; Cadiot, P. Tetrahedron Lett. 1982, 23, 5139. (b) Du Plessis, J. A. K.; Vosloo, H. C. M. J. Mol. Catal. 1991, 65, 51. (c) Kaneta, N.; Hirai, T.; Mori, M. Chem. Lett. 1995, 627. (d) Kaneta, N.; Hikichi, K.; Asaka, S.-I.; Uemura, M.; Mori, M. Chem. Lett. 1995, 1055.
18. For further optimizations and applications see: (a) Kloppenburg, L.; Song, D.; Bunz, U. H. F. J. Am. Chem. Soc. 1998, 120, 7973. (b) Pschirer, N. G. ; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481.
19. For further optimizations and applications see: (a) Kloppenburg, L.; Song, D.; Bunz, U. H. F. J. Am. Chem. Soc. 1998, 120, 7973. (b) Pschirer, N. G. ; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481.
20. Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 1734; Angew. Chem. 1998, 110, 1758.
21. Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 1734; Angew. Chem. 1998, 110, 1758.
22. (a) Fürstner, A.; Mathes, C.; Grela, K. Chem. Commun. 2001, 1057.
23. (b) Fürstner, A.; Grela, K. Angew. Chem. Int. Ed. 2000, 39, 1234; Angew. Chem. 2000, 112, 1292.
24. (b) Fürstner, A.; Grela, K. Angew. Chem. Int. Ed. 2000, 39, 1234; Angew. Chem. 2000, 112, 1292.
25. Fürstner, A.; Rumbo, A. J. Org. Chem. 2000, 65, 2608.
26. Schrock, R. R.; Clark, D. N.; Sancho, J.; Wengrovius, J. H.; Rocklage, S. M.; Pedersen, S. F. Organometallics 1982, 1, 1645.
27. Fürstner, A.; Mathes, C.; Lehmann, C. W. Chem.-Eur. J. 2001, 7, 5299.
28. (a) Gleiter, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 27; Angew. Chem. 1992, 104, 29.
29. (a) Gleiter, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 27; Angew. Chem. 1992, 104, 29.
30. (b) Gleiter, R.; Merger, R.; Treptow, B.; Wittwer, W.; Pflästerer, G. Synthesis 1993, 558.
31. Smith, W. N.; Beumel, O. F. Jr. Synthesis 1974, 441.
32. Gevorgyan, V.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 2001, 66, 2743.
33. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E. J. Am. Chem. Soc. 1989, 111, 3336.
34. Yost, D. M.; Osborne, D. W.; Garner, C. S. J. Am. Chem. Soc. 1941, 63, 3492.
35. Gleiter, R.; Ramming, M.; Weigl, H.; Wolfart, V.; Irngartinger, H.; Oeser, T. Liebigs Ann. Recueil 1997, 1545.
36. Dale, J. Angew. Chem., Int. Ed. Engl. 1966, 12, 1000; Angew. Chem. 1966, 78, 1070.
37. Dale, J. Angew. Chem., Int. Ed. Engl. 1966, 12, 1000; Angew. Chem. 1966, 78, 1070.
38. (a) Bhanu, S.; Scheinmann, F. J. Chem. Soc., Perkin Trans. 1 1979, 1218.
39. (b) Schill, G.; Keller, U. Synthesis 1972, 621.
40. Trost, B. M.; Matsuhara, S.; Caringi, J. J. J. Am. Chem. Soc. 1989, 111, 8745.
41. Matsuoka, T.; Negi, T.; Misumi, S. Synth. Commun. 1972, 2, 87.
42. Dale, J.; Hubert, A. J.; King, G. S. D. J. Chem. Soc. 1963, 73.
43. Henne, A. L.; Greenlee, K. W. J. Am. Chem. Soc. 1945, 67, 484.
44. Gunstone, F. D.; Sykes, P. J. J. Chem. Soc. 1962, 3055.
45. Hubert, A. J.; Dale, J. J. Chem. Soc. 1965, 3160.
46. Prelog, V.; Polyak, S. Helv. Chim. Acta 1957, 40, 816.
47. Hubert, A. J. J. Chem. Soc. C 1967, 2149.
48. (a) Sheldrick G. M.; SHELXTL-PLUS V5.10; Bruker Analytical X-ray-Division: Madison, WI, 1997;
49. (b) Methylated α,ω-diynes react under alkyne metathesis conditions to cyclic diynes.