Organic Letters
Letter
S. J.; O’Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature
ASSOCIATED CONTENT
Supporting Information
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011, 471, 461−466. (g) Keitz, B. K.; Endo, K.; Herbert, M. B.;
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S
Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 9686−9688. (h) Endo, K.;
Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 8525−8527. (i) Jiang, A. J.;
Zhao, Y.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131,
16630−16631. (j) Flook, M. M.; Jiang, A. J.; Schrock, R. R.; Muller, P.;
Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7962−7963. (k) Prunet, J.
Angew. Chem., Int. Ed. 2003, 42, 2826−2830.
Experimental details, procedures, compound characterization
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data, and copies of H and C spectra for all compounds,
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selected H spectra of the crude reaction mixture, selected
NOESY spectra, X-ray crystal structures (CIF) of compound
a-E, isomerization experiment of 3d-E, and DFT results of 3a-
3
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10) (a) Mizuta, Y.; Yasuda, K.; Obora, Y. J. Org. Chem. 2013, 78,
332−6337. (b) Marinescu, S. C.; Schrock, R. R.; Muller, P.; Takase,
M. K.; Hoveyda, A. H. Organometallics 2011, 30, 1780−1782.
c) Smitrovich, J. H.; Woerpel, K. A. J. Am. Chem. Soc. 1998, 120,
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AUTHOR INFORMATION
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12998−12999.
(11) (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc.
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002, 124, 11250−11251. (b) Tanaka, D.; Myers, A. G. Org. Lett.
Notes
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004, 6, 433−436. (c) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am.
Chem. Soc. 2005, 127, 10323−10333. (d) Hu, P.; Kan, J.; Su, W. P.;
Hong, M. C. Org. Lett. 2009, 11, 2341−2344. (e) Xie, K.; Yang, Z. Y.;
Zhou, X. J.; Li, X. J.; Wang, S. Z.; Tan, Z.; An, X. Y.; Guo, C. C. Org.
Lett. 2010, 12, 1564−1567. (f) Zhang, S. L.; Fu, Y.; Shang, R.; Guo, Q.
X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638−646. (g) Rodriguez, N.;
Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030−5048. (h) Xiang, S. H.;
Cai, S. T.; Zeng, J.; Liu, X. W. Org. Lett. 2011, 13, 4608−4611.
(i) Gigant, N.; Chausset-Boissarie, L.; Gillaizeau, I. Org. Lett. 2013, 15,
816−819. (j) Fardost, A.; Lindh, J.; Sjoberg, P. J. R.; Larhed, M. Adv.
Synth. Catal. 2014, 356, 870−878.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful to the Canada Research Chair (Tier 1)
foundation and NSERC for their support of our research. Dr.
Shu-Rong Ban acknowledges support from the Shanxi Scholar-
ship Council of China and Shanxi Medical University Program
of Training and Studying Abroad for Young Teachers.
REFERENCES
■
(
4
1) (a) Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698−
745. (b) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48,
4
(
621−4628.
2) de Medina, P.; Casper, R.; Savouret, J. F.; Poirot, M. J. Med.
Chem. 2005, 48, 287−291.
(
3) Simoni, D.; Invidiata, F. P.; Rondanin, R.; Grimaudo, S.;
Cannizzo, G.; Barbusca, E.; Porretto, F.; D’Alessandro, N.; Tolomeo,
M. J. Med. Chem. 1999, 42, 4961−4969.
(
4) (a) Stender, S.; Dyerberg, J. Ann. Nutr. Metab. 2004, 48, 61−66.
(
b) Mensink, R. P.; Katan, M. B. N. Engl. J. Med. 1990, 323, 439−445.
5) Kris-Etherton, P. M.; Harris, W. S.; Appel, L. J.; Nutrition, C.
Circulation 2002, 106, 2747−2757.
6) (a) Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.;
Mathison, C. J. N. J. Am. Chem. Soc. 2005, 127, 8872−8888.
b) Lipshutz, B. H.; Mollard, P.; Pfeiffer, S. S.; Chrisman, W. J. Am.
(
(
(
Chem. Soc. 2002, 124, 14282−14283. (c) Clemons, M.; Danson, S.;
Howell, A. Cancer Treat. Rev. 2002, 28, 165−180. (d) Suh, E. M.;
Kishi, Y. J. Am. Chem. Soc. 1994, 116, 11205−11206. (e) Takahashi,
A.; Kirio, Y.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc.
1
989, 111, 643−647. (f) Corey, E. J.; Weinshen, Nm; Schaaf, T. K.;
Huber, W. J. Am. Chem. Soc. 1969, 91, 5675−5677. (g) McMurry, J. E.;
Fleming, M. P. J. Am. Chem. Soc. 1974, 96, 4708−4709.
(
7) (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863−927.
(
b) Wadsworth, W.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83,
1
1
(
733−1738. (c) Wittig, G.; Schollkopf, U. Chem. Ber. Recl. 1954, 87,
318−1330.
8) (a) Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 4833−4836.
(
b) Keck, G. E.; Savin, K. A.; Weglarz, M. A. J. Org. Chem. 1995, 60,
3
2
194−3204. (c) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002,
563−2585. (d) Ono, K.; Yoshida, A.; Saito, N.; Fujishima, T.;
Honzawa, S.; Suhara, Y.; Kishimoto, S.; Sugiura, T.; Waku, K.;
Takayama, H.; Kittaka, A. J. Org. Chem. 2003, 68, 7407−7415.
(
e) Lebrun, M. E.; Le Marquand, P.; Berthelette, C. J. Org. Chem.
2
(
(
006, 71, 2009−2013.
9) (a) Quigley, B. L.; Grubbs, R. H. Chem. Sci. 2014, 5, 501−506.
b) Occhipinti, G.; Hansen, F. R.; Tornroos, K. W.; Jensen, V. R. J.
Am. Chem. Soc. 2013, 135, 3331−3334. (c) Cannon, J. S.; Grubbs, R.
H. Angew. Chem., Int. Ed. 2013, 52, 9001−9004. (d) Dang, Y. F.;
Wang, Z. X.; Wang, X. T. Organometallics 2012, 31, 8654−8657.
(
e) Peryshkov, D. V.; Schrock, R. R.; Takase, M. K.; Muller, P.;
Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 20754−20757. (f) Meek,
D
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