Organic Letters
Letter
(d) Liu, G.; Wu, Y. Top. Curr. Chem. 2010, 292, 195. (e) Jensen, T.;
Fristrup, P. Chem.Eur. J. 2009, 15, 9632.
V.; Gridnev, I. D.; Shevchenko, N. E.; Balenkova, E. S. Tetrahedron 1997,
53, 8173. For a review, see: (g) Nenajdenko, V. G.; Balenkova, E. S.
Russ. J. Org. Chem. 2003, 39, 323. For the development of Gin
glycosylation using sulfoxide/triflic anhydride combination, see:
(h) Garcia, B. A.; Poole, J. L.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119,
7597. (i) Di Bussolo, V.; Kim, Y.-J.; Gin, D. Y. J. Am. Chem. Soc. 1998,
120, 13515. (j) Di Bussolo, V.; Liu, J.; Huffman, J. L. G.; Gin, D. Y.
Angew. Chem., Int. Ed. 2000, 39, 204. (k) Garcia, B. A.; Gin, D. Y. J. Am.
Chem. Soc. 2000, 122, 4269. (l) Nguyen, H. M.; Poole, J. L.; Gin, D. Y.
Angew. Chem., Int. Ed. 2001, 40, 414. (m) Liu, J.; Gin, D. Y. J. Am. Chem.
Soc. 2002, 124, 9789. (n) Gin, D. Y. J. Carbohydr. Chem. 2002, 21, 645.
(o) Galonic, D. P.; Gin, D. Y. Nature 2007, 446, 1000. For a recent
review on mechanistically related Pummerer-type reactions, see:
(p) Smith, L. H. S.; Coote, S. C.; Sneddon, H. F.; Procter, D. J.
Angew. Chem., Int. Ed. 2010, 49, 5832.
(4) For one-pot procedures to realize asymmetric allylic C−H
functionalization, see: (a) Covell, D. J.; White, M. C. Angew. Chem., Int.
Ed. 2008, 47, 6448. (b) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2008,
130, 8590. (c) Zhao, B.; Du, H.; Fu, R.; Shi, Y. Org. Synth. 2010, 87, 263.
(d) Bao, H.; Tambar, U. K. J. Am. Chem. Soc. 2012, 134, 18495.
(e) Sharma, A.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 17983.
(f) Bao, H.; Bayeh, L.; Tambar, U. K. Angew. Chem., Int. Ed. 2014, 53,
1664.
(5) (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965,
6, 4387. (b) Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292.
(c) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395. (d) Trost,
B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (e) Mohr, J. T.; Stoltz,
B. M. Chem.Asian J. 2007, 2, 1476. (f) Lu, Z.; Ma, S. Angew. Chem., Int.
Ed. 2008, 47, 258.
1
(15) See Supporting Information for the crude H NMR and high
resolution mass spectrametry data for the corresponding allylic
sulfonium intermediate generated by mixing 1-phenylcycohexene
(1a), DMSO (2b), Tf2O, and then aqueous workup.
(6) Guillemonat, A. Ann. Chim. Appl. 1939, 11, 143.
(7) (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154.
(b) Arigoni, D.; Vasella, A.; Sharpless, K. B.; Jensenls, H. P. J. Am. Chem.
Soc. 1973, 95, 7917. (c) Jensen, H. P.; Sharpless, K. B. J. Org. Chem.
1975, 40, 264. (d) Stephenson, L. M.; Speth, D. R. J. Org. Chem. 1979,
44, 4683. (e) Singleton, D. A.; Hang, C. J. Org. Chem. 2000, 65, 7554.
(8) (a) Sharpless, K. B.; Hori, T.; Truesdale, L. K.; Dietrich, C. O. J. Am.
Chem. Soc. 1976, 98, 269. (b) Sharpless, K. B.; Hori, T. J. Org. Chem.
(16) For original works, see: (a) Bates, R. B.; Feld, D. Tetrahedron Lett.
1968, 9, 417. (b) Blackburn, G. M.; Ollis, W. D.; Plackett, J. D.; Smith,
C.; Sutherland, I. O. Chem. Commun. 1968, 186. (c) Baldwin, J. E.;
Hackler, R. E.; Kelly, D. P. Chem. Commun. 1968, 537−538. (d) Baldwin,
J. E.; Hackler, R. E.; Kelly, D. P. J. Am. Chem. Soc. 1968, 90, 4758. For
reviews, see: (e) Sulfur-Mediated Rearrangement II. In Topics in Current
Chemistry; Schaumann, E., Eds.; Springer: 2007. (f) Vedejs, E. Acc.
Chem. Res. 1984, 17, 358. (g) Vedejs, E. J. Org. Chem. 2004, 69, 5159.
(h) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. (i) Li, A.-H.;
Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. (j) Doyle, M. P.;
Forbes, D. C. Chem. Rev. 1998, 98, 911. (k) Zhang, Y.; Wang, J. Coord.
Chem. Rev. 2010, 254, 941.
(17) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J.
J. Am. Chem. Soc. 1997, 119, 6072.
(18) In a mechanistically related work, it was reported that when 4 was
treated with trifluoroacetic anhydride and then aquoeus NaHCO3, a
mixture of epoxide i and trifluoroacetate ii was obtained: Zhang, Y.; Lee,
J. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2011, 133, 752.
1976, 41, 176. (c) Schonberger, N.; Kresze, G. Justus Liebigs Ann. Chem.
̈
1975, 1975, 1725. (d) Kresze, G.; Muensterer, H. J. Org. Chem. 1983, 48,
3561. (e) Katz, T. J.; Shi, S. J. Org. Chem. 1994, 59, 8297. (f) Bruncko,
M.; Khuong, T.-A. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996,
35, 454.
(9) To the best of our knowledge, the work by Moiseenkov et al. was
the only precedent, which received virtually no citation since their
publication. (a) Veselovsky, V. V.; Dragan, V. A.; Moiseenkov, A. M.
Tetrahedron Lett. 1988, 29, 6637. (b) Moiseenkov, A. M.; Dragan, V. A.;
Veselovskii, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 365.
(10) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56.
(11) (a) Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am.
Chem. Soc. 2008, 130, 12901. (b) Young, A. J.; White, M. C. J. Am. Chem.
Soc. 2008, 130, 14090. (c) Hegedus, L. S.; Hayashi, T.; Darlington, W.
H. J. Am. Chem. Soc. 1978, 100, 7747.
(12) (a) Young, A. J.; White, M. C. Angew. Chem., Int. Ed. 2011, 50,
6824. (b) Trost, B. M.; Hansmann, M. M.; Thaisrivongs, D. A. Angew.
Chem., Int. Ed. 2012, 51, 4950. (c) Trost, B. M.; Thaisrivongs, D. A.;
Hansmann, M. M. Angew. Chem., Int. Ed. 2012, 51, 11522. (d) Trost, B.
M.; Thaisrivongs, D. A.; Donckele, E. J. Angew. Chem., Int. Ed. 2013, 52,
1523. (e) Li, L.; Chen, Q.-Y.; Guo, Y. Chem. Commun. 2013, 49, 8764.
(f) Howell, J. M.; Liu, W.; Young, A. J.; White, M. C. J. Am. Chem. Soc.
2014, 136, 5750. (g) Wang, G.-W.; Zhou, A.-X.; Li, S.-X.; Yang, S.-D.
Org. Lett. 2014, 16, 3118. (h) Tang, S.; Wu, X.; Liao, W.; Liu, K.; Liu, C.;
Luo, S.; Lei, A. Org. Lett. 2014, 16, 3584. (i) Wang, P.-S.; Lin, H.-C.;
Zhai, Y.-J.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53,
12218. (j) Engelin, C.; Jensen, T.; Rodriguez-Rodriguez, S.; Fristrup, P.
ACS Catal. 2013, 3, 294.
(19) Yu, B.; Liu, A.-H.; He, L.-N.; Li, B.; Diao, Z.-F.; Li, Y.-N. Green
Chem. 2012, 14, 957.
(13) For other mechanistically related work on allylic C−H
trifluorometylation, arylation, or carbonylation reactions, see: (a) Par-
sons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120.
(b) Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.;
Liu, L. J. Am. Chem. Soc. 2011, 133, 15300. (c) Wang, X.; Ye, Y.; Zhang,
S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133,
16410. (d) Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106. (e) Sekine, M.;
Ilies, L.; Nakamura, E. Org. Lett. 2013, 15, 714. (f) Jiang, H.; Yang, W.;
Chen, H.; Li, J.; Wu, W. Chem. Commun. 2014, 50, 7202. (g) Chen, H.;
Cai, C.; Liu, X.; Li, X.; Jiang, H. Chem. Commun. 2011, 47, 12224.
(14) For selected early examples using sulfoxide/triflic anhydride
combination, see: (a) Hendrickson, J. B.; Schwartzman, S. M.
Tetrahedron Lett. 1975, 273. (b) Kahne, D.; Walker, S.; Cheng, Y.;
Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881. (c) Umemoto, T.;
Ishihara, S. J. Am. Chem. Soc. 1993, 115, 2156. (d) Yan, L.; Kahne, D. J.
Am. Chem. Soc. 1996, 118, 9239. (e) Corey, E. J.; Gin, D. Y.; Kania, R. S.
J. Am. Chem. Soc. 1996, 118, 9202. (f) Nenajdenko, V. G.; Vertelezkij, P.
D
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