Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: Mechanistic aspects and applications to natural product synthesis

Angewandte Chemie - International Edition

Volumn 52, Issue 32, 2013, Pages 8395-8400

  Mann, Tyler J ^a   Speed, Alexander W H ^a   Schrock, Richard R ^b   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

allylic ethers; cross metathesis; molybdenum; olefin metathesis; Z olefins

Indexed keywords

ALLYLIC ETHERS; BENZYL ETHERS; CROSS METATHESIS; CROSS-COUPLINGS; MECHANISTIC ASPECTS; NATURAL PRODUCT SYNTHESIS; OLEFIN METATHESIS; PYRROLIDE;

MOLYBDENUM; OLEFINS;

ETHERS;

BIOLOGICAL PRODUCT; ETHER DERIVATIVE; MOLYBDENUM; ORGANOMETALLIC COMPOUND;

ALLYLIC ETHERS; ARTICLE; CATALYSIS; CHEMISTRY; CROSS-METATHESIS; OLEFIN METATHESIS; SYNTHESIS; Z OLEFINS;

ALLYLIC ETHERS; CROSS-METATHESIS; MOLYBDENUM; OLEFIN METATHESIS; Z OLEFINS;

BIOLOGICAL PRODUCTS; CATALYSIS; ETHERS; ORGANOMETALLIC COMPOUNDS;

EID: 84882287440     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302538     Document Type: Article

References (45)

1. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370
2. A. Lumbroso, M. L. Cooke, B. Breit, Angew. Chem. 2013, 125, 1942-1986
3. Angew. Chem. Int. Ed. 2013, 52, 1890-1932.
4. H. Ohmiya, U. Yokobori, Y. Makida, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 2895-2897
5. H. Ohmiya, N. Yokokawa, M. Sawamura, Org. Lett. 2010, 12, 2438-2440.
6. Y. Shido, M. Yoshida, M. Tanabe, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 18573-18576.
7. M. Takahashi, M. McLaughlin, G. C. Micalizio, Angew. Chem. 2009, 121, 3702-3706
8. Angew. Chem. Int. Ed. 2009, 48, 3648-3652
9. M. Z. Chen, M. McLaughlin, M. Takahashi, M. A. Tarselli, D. Yang, S. Umemura, G. C. Micalizio, J. Org. Chem. 2010, 75, 8048-8059
10. D. Yang, G. C. Micalizio, J. Am. Chem. Soc. 2011, 133, 9216-9219
11. D. Yang, G. C. Micalizio, J. Am. Chem. Soc. 2012, 134, 15237-15240.
12. S. Mitsui, K. Torii, H. Fukui, K. Tsujimura, A. Maeda, M. Nose, A. Nagatsu, H. Mizukami, A. Morita, J. Pharmacol. Exp. Ther. 2010, 333, 954-960
13. P. Wyrembek, R. Negri, P. Kaczor, M. Czyzewska, G. Appendino, J. W. Mozrzymas, J. Nat. Prod. 2012, 75, 610-616; for determination of absolute stereochemistry (through Ru-catalyzed ethenolysis of the Z alkene), see
14. A. S. Ratnayake, T. Hemscheidt, Org. Lett. 2002, 4, 4667-4669
15. S. Tamura, T. Ohno, Y. Hattori, N. Murakami, Tetrahedron Lett. 2010, 51, 1523-1525.
16. M. Kobaisy, Z. Abramowitz, L. Lermer, G. Saxena, R. E. W. Hancock, G. H. N. Towers, D. Doxsee, R. W. Stokes, J. Nat. Prod. 1997, 60, 1210-1213
17. J.-H. Liu, S. Zschocke, R. Bauer, Phytochemistry 1998, 49, 211-213
18. V. M. Dembitsky, Lipids 2006, 41, 883-924.
19. A. K. Chatterjee, in Handbook of Metathesis, Vol. 1 (Ed.:, R. H. Grubbs,), Wiley-VCH, Weinheim, 2003, pp. 246-295
20. S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968
21. Angew. Chem. Int. Ed. 2003, 42, 1900-1923
22. J. Prunet, L. Grimaud, in Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts (Eds.:, J. Cossy, S. A. Arseniyades, C. Meyer,), Wiley-VCH, Weinheim, 2010, pp. 287-312.
23. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251
24. C. Samojłowicz, M. Bieniek, K. Grela, Chem. Rev. 2009, 109, 3708-3742
25. G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev. 2010, 110, 1746-1787
26. A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem. 2010, 122, 38-49
27. Angew. Chem. Int. Ed. 2010, 49, 34-44.
28. S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461-466; for related studies, see
29. I. Ibrahem, M. Yu, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 3844-3845
30. M. Yu, I. Ibrahem, M. Hasegawa, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 2788-2799
31. E. T. Kiesewetter, R. V. O'Brien, E. C. Yu, S. J. Meek, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2013, 135, 6026.
32. For a comprehensive review on stereoselective synthesis of Z alkenes, see:, W.-Y. Siau, Y. Zhang, Y. Zhao, Top. Curr. Chem. 2012, 327, 33-58.
33. K. Endo, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 8525-8527
34. B. K. Keitz, K. Endo, P. R. Patel, M. B. Herbert, R. H. Grubbs, J. Am. Chem. Soc. 2012, 134, 693-699
35. M. B. Herbert, V. M. Marx, R. L. Pederson, R. H. Grubbs, Angew. Chem. 2013, 125, 328-332
36. Angew. Chem. Int. Ed. 2013, 52, 310-314; for related Ru-catalyzed Z-selective olefin metathesis reactions, see
37. R. K. M. Khan, R. V. O'Brien, S. Torker, B. Li, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 12774-12779
38. G. Occhipinti, F. R. Hansen, K. W. Törnroos, V. R. Jensen, J. Am. Chem. Soc. 2013, 135, 3331-3334.
39. M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature 2011, 479, 88-93
40. C. Wang, M. Yu, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Chem. Eur. J. 2013, 19, 2726-2740.
41. R. R. Schrock, Chem. Rev. 2009, 109, 3211-3226.
42. In complexes represented by B-D, the electron density at the alkylidene C is stabilized by the adjacent electron-withdrawing C-O bond, which lowers the catalytic activity. See:, D. S. La, E. S. Sattely, J. G. Ford, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 7767-7778.
43. T. Řezanka, V. M. Dembitsky, Tetrahedron 2001, 57, 8743-8749.
44. S. Hwang, J. H. Kim, H. S. Kim, S. Kim, Eur. J. Org. Chem. 2011, 7414-7418
45. B. M. Trost, A. Quintard, Org. Lett. 2012, 14, 4698-4700. Further details are provided in the Supporting Information.