New tandem catalysis: Preparation of cyclic enol ethers through a ruthenium-catalyzed ring-closing metathesis-olefin isomerization sequence

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13390-13391

  Sutton, Amanda E ^a   Seigal, Benjamin A ^a   Finnegan, David F ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; ETHER DERIVATIVE; RUTHENIUM; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ISOMERISM; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0037073212     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028044q     Document Type: Article

References (46)

1. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
2. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
3. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
4. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
5. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
6. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
7. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
8. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
9. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
10. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
11. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
12. For recent examples of tandem processes, see: (a) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305. (b) Molander, G. A.; Brown, G. A.; Storch de Gracia, I. J Org. Chem. 2002, 67, 3459. (c) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Eur. J. 2002, 8, 1719. (d) Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552. (e) Murakami, M.; Ubukata, M.; Ito, Y. Chem. Lett. 2002, 294. For recent reviews. see: (f) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 3, 227. (g) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237. (h) Waldmann, H. Org. Synth. Highlights II 1995, 193. (i) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (j) Winkler, J. D. Chem. Rev. 1996, 96, 167. (k) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195. (l) Bunce, R. A. Tetrahedron 1995, 51, 13103.
13. (a) Fürstner, A. Angew. Chem., Int. Ed. 2000. 39, 3012.
14. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
15. (a) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872. (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196. For an overview of ruthenium-catalyzed reactions, see: (c) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599. (d) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev., 2001, 101, 2067.
16. (a) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872. (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196. For an overview of ruthenium-catalyzed reactions, see: (c) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599. (d) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev., 2001, 101, 2067.
17. (a) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872. (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196. For an overview of ruthenium-catalyzed reactions, see: (c) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599. (d) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev., 2001, 101, 2067.
18. (a) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872. (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196. For an overview of ruthenium-catalyzed reactions, see: (c) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599. (d) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev., 2001, 101, 2067.
19. (a) Hu, Y.-J.; Dominique, R.; Das, S. K.; Roy, R. Can. J. Chem. 2000, 78, 838.
20. (b) Cadot, C.; Dalko, P. I.; Cossy, J. Tetrahedron Lett. 2002, 43, 1839.
21. (c) Fürstner, A.; Theil, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
22. (d) Hoye, T. R.; Zhao, H. Org. Lett. 1999, 1, 1123.
23. (e) Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635.
24. (f) Nakashima, K.; Ito, R.; Sono, M.; Tori, M. Heterocycles 2000, 53, 301.
25. (g) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781.
26. Please see Supporting Information for the purification procedure of the commercially available catalyst.
27. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
28. (a) Clark, J. S.; Kettle, J. G. Tetrahedron 1999, 55, 8231.
29. (b) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
30. Magnus, P.; Roe, M. B. Tetrahedron Lett. 1996, 37, 303.
31. Armstrong, S. K. J. Chem. Soc. Perkin Trans. 1 1998, 371.
32. Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335.
33. (a) Rainer, J. D.; Cox, J. M.: Allwein, S. P. Tetrahedron Lett. 2001, 42, 179.
34. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
35. (c) Arisawa, M.; Theerladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029.
36. (d) Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001. 42, 8023.
37. (e) Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623.
38. Clark, J. S.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973 and references therein.
39. Previously, such an approach has been conducted in separate steps utilizing 1 for the RCM and Wilkinson's catalyst for the olefin isomerization. Leeuwenburgh, M. A.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Synlett 1997, 11, 1263.
40. The 95:5 nitrogen:hydrogen mixture (Forming Gas) is typically used for glovebox catalyst regeneration (AGA Specialty Gases, no. 7867, industrial grade).
41. The isolated yields are competitive with other methods to prepare enol ethers. For example, see: Boschi, A.; Chiappe, C.; De Rubertis, A.; Ruasse, M. F. J. Org. Chem. 2000, 65, 8470.
42. For an example of RCM on an enamine, see: Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. S.; Hiemstra. H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045. For a related RCM-isomerization example (reported as an undesired byproduct), see: Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628.
43. For an example of RCM on an enamine, see: Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. S.; Hiemstra. H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045. For a related RCM-isomerization example (reported as an undesired byproduct), see: Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628.
44. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
45. For examples of forming ruthenium hydrides through hydrogenation of ruthenium alkylidenes, see: (a) Oliván, M.; Caulton, K. G. Inorg. Chem. 1999, 38, 566.
46. (b) Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Inorg. Chem. 2000, 39, 5412.