Journal of the American Chemical Society
Article
Synthesis 2011, 1988. (d) Hashimoto, T.; Omote, M.; Maruoka, K.
K. Bull. Chem. Soc. Jpn. 1985, 58, 397. (g) Shimizu, T.; Hayashi, Y. Y.;
Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277. (h) Griffith, A.
K.; Vanos, C. M.; Lambert, T. H. J. Am. Chem. Soc. 2012, 134, 18581.
(i) Davis, L. O.; Daniel, W. F. M.; Tobey, S. L. Tetrahedron Lett. 2012,
53, 522. (j) Lin, G.-Q.; Lei, X.; Liu, P.; Xu, Q.-Q.; Dong, C. Synlett
2012, 23, 2087.
́
Angew. Chem., Int. Ed. 2011, 50, 3489. (e) Fernandez, M.; Reyes, E.;
Vicario, J. L.; Badía, D.; Carrillo, L. Adv. Synth. Catal. 2012, 354, 371.
(f) Hashimoto, T.; Kimura, H.; Kawamata, Y.; Maruoka, K. Nat. Chem.
2011, 3, 642. (g) Deiana, L.; Zhao, G.-L.; Leijonmarck, H.; Sun, J.;
Lehmann, C. W.; Cor
S.; List, B. Angew. Chem., Int. Ed. 2009, 48, 9975.
(7) Rueping, M.; Maji, M. S.; Kucuk, H. B.; Atodiresei, I. Angew.
́
dova, A. ChemistryOpen 2012, 1, 134. (h) Muller,
̈
(13) The absolute configuration at the C3 stereocenter was assigned
in analogy to our previously reported compounds.7
̧
̈
̈
Chem., Int. Ed. 2012, 51, 12864.
(14) Detailed experimental results with other thioethers are included
in Supporting Information.
(8) For related work in the field of chiral BINOL-based N-
triflylphosphoramides, see: (a) Yamamoto, S. A.; Nakashima, D.;
Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626. For an overview,
see: (b) Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W.; Atodiresei, I.
Angew. Chem., Int. Ed. 2011, 50, 6706. For further examples, see:
(c) Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J.
Angew. Chem., Int. Ed. 2007, 46, 2097. (d) Rueping, M.; Nachtsheim,
B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593.
(e) Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew.
Chem., Int. Ed. 2008, 47, 6798. (f) Enders, D.; Narine, A. A.; Toulgoat,
F.; Bisschops, T. Angew. Chem., Int. Ed. 2008, 47, 5661. (g) Zeng, M.;
Kang, Q.; He, Q.-L.; You, S.-L. Adv. Synth. Catal. 2008, 350, 2169.
(h) Rueping, M.; Ieawsuwan, W. Adv. Synth. Catal. 2009, 351, 78.
(i) Rueping, M.; Nachtsheim, B. J.; Koenigs, R. M.; Ieawsuwan, W.
Chem.Eur. J. 2010, 16, 13116. (j) Rueping, M.; Lin, M.-Y. Chem.
Eur. J. 2010, 16, 4169. (k) Rueping, M.; Nachtsheim, B. J. Synlett 2010,
119. (l) Rueping, M.; Merino, E.; Koenigs, R. M. Adv. Synth. Catal.
2010, 352, 2629. (m) Cheon, C. H.; Yamamoto, H. Org. Lett. 2010,
12, 2476. (n) Rueping, M.; Uria, U.; Lin, M.-Y.; Atodiresei, I. J. Am.
Chem. Soc. 2011, 133, 3732. (o) Hashimoto, T.; Nakatsu, H.;
Yamamoto, K.; Maruoka, K. J. Am. Chem. Soc. 2011, 133, 9730.
(p) Rueping, M.; Ieawsuwan, W. Chem. Commun. 2011, 47, 11450.
(9) For SPINOL-derived phosphoric acid catalysts, see: (a) Jia, Y.-X.;
Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem., Int. Ed.
2007, 46, 5565. (b) Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41,
581. (c) Coric, I.; Muller, S.; List, B. J. Am. Chem. Soc. 2010, 132,
17370. (d) Xing, C.-H.; Liao, Y.-X.; Ng, J.; Hu, Q.-S. J. Org. Chem.
2011, 76, 4125. (e) Xu, B.; Zhu, S.-F.; Xie, X.-L.; Shen, J.-J.; Zhou, Q.-
L. Angew. Chem., Int. Ed. 2011, 50, 11483. (f) Xing, C.-H.; Liao, Y.-X.;
Ng, J.; Hu, Q.-S. J. Org. Chem. 2011, 76, 4125. (g) Huang, D.; Xu, F.;
Lin, X.; Wang, Y. Chem.Eur. J. 2012, 18, 3148. (h) Huang, D.; Xu,
F.; Chen, T.; Wang, Y.; Lin, X. RSC Adv. 2013, 3, 573. (i) Zhao, Y.; Li,
X.; Mo, F.; Li, L.; Lin, X. RSC Adv. 2013, 3, 11895. (j) Huang, D.; Li,
X.; Xu, F.; Li, L.; Lin, X. ACS Catal. 2013, 3, 2244. (k) Xu, B.; Zhu, S.-
F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5,
1442. (l) Wang, S.-G.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 2194.
(m) Xu, B.; Zhu, S.-F.; Zuo, X.-D.; Zhang, Z.-C.; Zhou, Q.-L. Angew.
Chem., Int. Ed. 2014, 53, 3913.
(15) The reaction tolerates various alkyl substituents on vinyl ethers
with moderate to high enantioselectivities, and the ethyl vinyl ether
gives the highest yield:
Also, the reaction with 2,3-dihydrofuran gives racemic products,
and the reaction with 3,4-dihydro-2H-pyran does not produce
the desired cycloadduct.
(16) The reactions with enamides only give racemic products or no
desired cycloadducts:
(17) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,
B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.
P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.;
Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,
T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.;
Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin,
K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.;
Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega,
N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.;
Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.;
Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.;
Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.;
Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.;
Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09,
revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
(18) (a) Zhao, Y.; Truhlar, D. Theor. Chem. Acc. 2008, 120, 215.
(b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157.
(19) (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
(b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem.
2003, 24, 669. (c) Takano, Y.; Houk, K. N. J. Chem. Theory Comput.
2005, 1, 70.
(20) There is an unfavorable regio-isomer for each complex in Figure
1; the structures and relative Gibbs free energies are shown in
Supporting Information.
(10) Kaupmees, K.; Tolstoluzhsky, N.; Raja, S.; Rueping, M.; Leito, I.
Angew. Chem., Int. Ed. 2013, 51, 11569.
(11) (a) Domingo, L. R. Eur. J. Org. Chem. 2000, 2265. (b) Tanaka,
J.; Kanemasa, S. Tetrahedron 2001, 57, 899. (c) Wagner, G. Chem.
Eur. J. 2003, 9, 1503. (d) Kuznetsov, M. L.; Kukushkin, V. Y.; Haukka,
M.; Pombeiro, A. J. L. Inorg. Chim. Acta 2003, 356, 85. (e) Castillo, R.;
Andres, J.; Domingo, L. R. Eur. J. Org. Chem. 2005, 4705. (f) Domingo,
́
L. R.; Benchouk, W.; Mekelleche, S. M. Tetrahedron 2007, 63, 4464.
(g) Wagner, G.; Danks, T. N.; Vullo, V. Tetrahedron 2007, 63, 5251.
(h) Badoiu, A.; Bernardinelli, G.; Mareda, J.; Kundig, E. P.; Viton, F.
̃
̈
Chem.Asian J. 2008, 3, 1298. (i) Wagner, G.; Danks, T. N.; Desai, B.
́
Tetrahedron 2008, 64, 477. (j) Frank, E.; Mucsi, Z.; Szec
I.; Wolfling, J.; Schneider, G. New J. Chem. 2010, 34, 2671.
(k) Chaudhuri, T.; Banerjee, M. J. Luminescence 2012, 132, 1456.
(l) Sniezek, M.; Stecko, S.; Panfil, I.; Furman, B.; Urban
́
si, M.; Zupko,
́
̈
́
czyk-
̇
Lipkowska, Z.; Chmielewski, M. Tetrahedron: Asymmetry 2013, 24, 89.
(12) (a) Hesse, K.-D. Justus Liebigs Ann. Chem. 1970, 743, 50. (b) Le
Fevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821.
(c) Wilson, R. M.; Rekers, J. W. J. Am. Chem. Soc. 1979, 101, 4005.
(d) Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22,
1333. (e) Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull.
Chem. Soc. Jpn. 1982, 55, 2456. (f) Shimizu, T.; Hayashi, Y.; Teramura,
13779
dx.doi.org/10.1021/ja506660c | J. Am. Chem. Soc. 2014, 136, 13769−13780