Organic Letters
ORCID
Letter
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank the NIH (R01GM071779) for financial support.
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REFERENCES
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(1) (a) Heaney, H. Chem. Rev. 1962, 62, 81. (b) Reinecke, M. G.
Tetrahedron 1982, 38, 427. (c) Pellissier, H.; Santelli, M. Tetrahedron
2003, 59, 701. (d) Wenk, H. H.; Winkler, M.; Sander, W. Angew.
Chem., Int. Ed. 2003, 42, 502. (e) Tadross, P. M.; Stoltz, B. M. Chem.
Rev. 2012, 112, 3550.
(2) (a) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047.
(b) Suzuki, N. Yuki Gosei Kagaku Kyokaishi 2007, 65, 347. (c) Sletten,
E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974.
(d) Gampe, C. M.; Boulos, S.; Carreira, E. M. Angew. Chem., Int. Ed.
2010, 49, 4092. (e) Gampe, C. M.; Carreira, E. M. Angew. Chem., Int.
Ed. 2011, 50, 2962. (f) Gampe, C. M.; Carreira, E. M. Chem. - Eur. J.
2012, 18, 15761. (g) Gampe, C. M.; Carreira, E. M. Angew. Chem., Int.
Ed. 2012, 51, 3766. (h) Yoshida, S.; Karaki, F.; Uchida, K.; Hosoya, T.
Chem. Commun. 2015, 51, 8745.
(3) (a) Scardiglia, F.; Roberts, J. D. Tetrahedron 1957, 1, 343.
(b) Wittig, G.; Pohlke, R. Chem. Ber. 1961, 94, 3276. (c) Montgomery,
L. K.; Scardiglia, F.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 1917.
(4) Hioki, Y.; Okano, K.; Mori, A. Chem. Commun. 2017, 53, 2614.
(5) Willey, F. G. Angew. Chem., Int. Ed. 1964, 94, 3276.
(6) Al-Omari, M.; Banert, K.; Hagedorn, M. Angew. Chem., Int. Ed.
2006, 45, 309.
(7) (a) Atanes, N.; Escudero, S.; Perez, D.; Guitian, E.; Castedo, L.
Tetrahedron Lett. 1998, 39, 3039. (b) Medina, J. M.; McMahon, T. C.;
Jimenez-Oses, G.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2014,
136, 14706. (c) McMahon, T. C.; Medina, J. M.; Yang, Y.-F.;
Simmons, B. J.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2015, 137,
4082. (d) Barber, J. S.; Styduhar, E. D.; Pham, H. V.; McMahon, T.
C.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2016, 138, 2512.
(8) Fujita, M.; Sakanishi, Y.; Kim, W. H.; Okuyama, T. Chem. Lett.
2002, 31, 908.
(9) Devlin, A. S.; Du Bois, J. Chem. Sci. 2013, 4, 1059.
(10) (a) Stang, P. J. Vinyl Cations. Vinyl Cations; Academic Press:
1979; p 515. (b) Nefedov, V. D.; Sinotova, E. N.; Lebedev, V. P. Russ.
Chem. Rev. 1992, 61, 523.
(11) Fittig, R.; Schrohe, A. Chem. Ber. 1875, 8, 367.
(12) Jacobs, T. L.; Searles, S. J. Am. Chem. Soc. 1944, 66, 686.
(13) Grob, C. A.; Cseh, G. Helv. Chim. Acta 1964, 47, 194.
(14) (a) Subramanian, L. R.; Hanack, M. Chem. Ber. 1972, 105,
1465. (b) Summerville, R. H.; Schleyer, P. V. R. J. Am. Chem. Soc.
1974, 96, 1110. (c) Hanack, M. Acc. Chem. Res. 1976, 9, 364.
(d) Stang, P. J. Acc. Chem. Res. 1978, 11, 107.
́
̃
anas, F. J.; Rodríguez, F. Chem.
(15) (a) Alonso, P.; Pardo, P.; Fan
Commun. 2014, 50, 14364. (b) Alonso, P.; Pardo, P.; Galvan, A.;
́
́
Fananas, F. J.; Rodríguez, F. Angew. Chem., Int. Ed. 2015, 54, 15506.
̃
(16) Inaba, K.; Takaya, J.; Iwasawa, N. Chem. Lett. 2007, 36, 474.
(17) Vasilyev, A. V. Russ. Chem. Rev. 2013, 82, 187.
(18) Substrates substituted at the ortho and meta positions were
recalcitrant to the cationic cyclization, with the exception of
compounds 5e and 8. For the structures of the failed substrates,
(19) (a) Kuhnt, M.; Rimpler, H.; Heinrich, M. Phytochemistry 1994,
36, 485. (b) Maeda, K.; Hamada, T.; Onitsuka, S.; Okamura, H. J.
Nat. Prod. 2017, 80, 1446.
(20) Hamada, T.; White, Y.; Nakashima, M.; Oiso, Y.; Fujita, M. J.;
Okamura, H.; Iwagawa, T.; Arima, N. Molecules 2012, 17, 9931.
̈
(21) Masters, K.-S.; Wallesch, M.; Brase, S. J. Org. Chem. 2011, 76,
9060.
(22) Boukouvalas, J.; Thibault, C. J. Org. Chem. 2015, 80, 681.
D
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