Organic Letters
Letter
Teraoka, K.; Uekusa, H.; Nakazono, K.; Takata, T.; Tanaka, K. Chem. -
Eur. J. 2016, 22, 14190. (c) Doulcet, J.; Stephenson, G. R. Chem. - Eur. J.
2015, 21, 18677. (d) Doulcet, J.; Stephenson, G. R. Chem. - Eur. J. 2015,
21, 13431. (e) Nakamura, K.; Furumi, S.; Takeuchi, M.; Shibuya, T.;
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Tanaka, K. J. Am. Chem. Soc. 2014, 136, 5555. (f) Kotzner, L.; Webber,
̈
M. J.; Martínez, A.; DeFusco, C.; List, B. Angew. Chem., Int. Ed. 2014, 53,
Notes
5202. (g) Grandbois, A.; Collins, S. K. Chem. - Eur. J. 2008, 14, 9323.
(h) Caeiro, J.; Pena, D.; Cobas, A.; Per
́
ez, D.; Guitian
Catal. 2006, 348, 2466. (i) Miyasaka, M.; Rajca, A.; Pink, M.; Rajca, S. J.
Am. Chem. Soc. 2005, 127, 13806. (j) Carreno, M. C.; Gonzalez-Lopez,
́
, E. Adv. Synth.
̃
The authors declare no competing financial interest.
́
́
̃
M.; Urbano, A. Chem. Commun. 2005, 611. (k) Rajca, A.; Miyasaka, M.;
ACKNOWLEDGMENTS
Pink, M.; Wang, H.; Rajca, S. J. Am. Chem. Soc. 2004, 126, 15211.
■
(l) Carreno, M.C.; García-Cerrada, S.; Urbano, A. Chem. - Eur. J. 2003, 9,
̃
This work was supported in part by ACT-C from JST (Japan)
and a Grant-in-Aid for Scientific Research (No. 26102004) from
MEXT (Japan). We thank the Natural Science Center for Basic
Research and Development (N-BARD), Hiroshima University,
for the measurement of CPL using JASCO CPL-200 and Prof.
Toshikazu Takata and Dr. Kazuko Nakazono (Tokyo Institute of
Technology) for the measurement of ECD. We also thank
Takasago International Corporation for the gift of H8-BINAP
and Segphos, Umicore for generous support in supplying the
rhodium and palladium complexes, and Central Glass Co., Ltd.,
for the gift of trifluoromethanesulfonic anhydride.
4118.
(8) For the asymmetric synthesis of helicenes and helicene-like
molecules via diastereoselective [2 + 2 + 2] cycloaddition, see:
̌
(a) Sehnal, P.; Stara,
Rulísek, L.; Chocholouso
Císarova, I.; Stary, I. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 13169.
(b) Samal, M.; Chercheja, S.; Rybac
J.; Bednarova, L.; Saman, D.; Stara, I. G.; Stary, I. J. Am. Chem. Soc. 2015,
137, 8469.
́
I. G.; Saman, D.; Tichy, M.; Míse
̌
k, J.; Cvack
̌
a, J.;
́
̌
̌
va, J.; Vacek, J.; Goryl, G.; Szymonski, M.;
́
̌
́
́
́
́
ek, J.; Chocholousova, J. V.; Vacek,
́
́
́
(9) For other recent examples of the diastereoselective synthesis of
helicenes and helicene-like molecules, see: (a) Kaneko, E.; Matsumoto,
Y.; Kamikawa, K. Chem. - Eur. J. 2013, 19, 11837. (b) Lin, A.; Dou, G.-L.;
Hu, M.-H.; Cao, C.-P.; Huang, Z.-B.; Shi, D.-Q. Org. Lett. 2013, 15,
1238.
(10) Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K.; Lee, S. J. Org. Chem.
2010, 75, 6244.
(11) (a) Ireland, R. E.; Walba, D. M. Org. Synth. 1977, 56, 44.
(b) Arichi, N.; Hata, K.; Takemoto, Y.; Yamada, K.; Yamaoka, Y.;
Takasu, K. Tetrahedron 2015, 71, 233.
REFERENCES
■
(1) For reviews, see: (a) Tanaka, K.; Kimura, Y.; Murayama, K. Bull.
Chem. Soc. Jpn. 2015, 88, 375. (b) Transition-Metal-Mediated Aromatic
Ring Construction; Tanaka, K., Ed.; Wiley: Hoboken, 2013; Chapter 10.
(c) Peng, Z.; Takenaka, N. Chem. Rec. 2013, 13, 28. (d) Shen, Y.; Chen,
C.-F. Chem. Rev. 2012, 112, 1463. (e) Amemiya, R.; Yamaguchi, M.
Chem. Rec. 2008, 8, 116. (f) Rajca, A.; Miyasaka, M. In Functional
(12) Tsuji, J.; Takahashi, M.; Takahashi, T. Tetrahedron Lett. 1980, 21,
849.
(13) For the optimization of reaction conditions for 1c and 1d, see
Organic Materials: Syntheses, Strategies, and Applications; Muller, T. T. J.,
̈
Bunz, U. H. F., Eds.; Wiley-VCH: Weinheim, 2007; p 543. (g) Nuckolls,
C.; Shao, R.; Jang, W.-G.; Clark, N. A.; Walba, D. M.; Katz, T. J. Chem.
Mater. 2002, 14, 773. (h) Katz, T. J. Angew. Chem., Int. Ed. 2000, 39,
1921.
(15) For selected recent examples of CPL of a small organic molecular
system, see: (a) Alnoman, R. B.; Rihn, S.; O’Connor, D. C.; Black, F. A.;
Costello, B.; Waddell, P. G.; Clegg, W.; Peacock, R. D.; Herrebout, W.;
Knight, J. G.; Hall, M. J. Chem. - Eur. J. 2016, 22, 93. (b) Gon, M.;
Morisaki, Y.; Sawada, R.; Chujo, Y. Chem. - Eur. J. 2016, 22, 2291.
(c) Sakai, H.; Kubota, T.; Yuasa, J.; Araki, Y.; Sakanoue, T.; Takenobu,
T.; Wada, T.; Kawai, T.; Hasobe, T. J. Phys. Chem. C 2016, 120, 7860.
(d) Goto, K.; Yamaguchi, R.; Hiroto, S.; Ueno, H.; Kawai, T.;
Shinokubo, H. Angew. Chem., Int. Ed. 2012, 51, 10333. (e) Maeda, H.;
Bando, Y.; Shimomura, K.; Yamada, I.; Naito, M.; Nobusawa, K.;
Tsumatori, H.; Kawai, T. J. Am. Chem. Soc. 2011, 133, 9266.
(f) Kaseyama, T.; Furumi, S.; Zhang, X.; Tanaka, K.; Takeuchi, M.
Angew. Chem., Int. Ed. 2011, 50, 3684. (g) Tsumatori, H.; Nakashima, T.;
Kawai, T. Org. Lett. 2010, 12, 2362. See also refs 3d and 7e.
(16) (a) Vander Donckt, E. V.; Nasielski, J.; Greenleaf, J. R.; Birks, J. B.
Chem. Phys. Lett. 1968, 2, 409. (b) Martin, R. H.; Marchant, M. J.
Tetrahedron 1974, 30, 343.
(2) For a review, see: Transition-Metal-Mediated Aromatic Ring
Construction; Tanaka, K., Ed.; Wiley: Hoboken, 2013.
(3) For the rhodium(I) catalysis, see: (a) Tanaka, K.; Kamisawa, A.;
Suda, T.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007, 129, 12078.
(b) Tanaka, K.; Fukawa, N.; Suda, T.; Noguchi, K. Angew. Chem., Int. Ed.
2009, 48, 5470. (c) Fukawa, N.; Osaka, T.; Noguchi, K.; Tanaka, K. Org.
Lett. 2010, 12, 1324. (d) Sawada, Y.; Furumi, S.; Takai, A.; Takeuchi, M.;
Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2012, 134, 4080. (e) Kimura,
Y.; Fukawa, N.; Miyauchi, Y.; Noguchi, K.; Tanaka, K. Angew. Chem., Int.
Ed. 2014, 53, 8480. (f) Murayama, K.; Oike, Y.; Furumi, S.; Takeuchi,
M.; Noguchi, K.; Tanaka, K. Eur. J. Org. Chem. 2015, 2015, 1409.
(4) For nickel(0) catalysis, see: (a) Stara,
́
I. G.; Stary, I.; Kollar
́
ovic,
̌
A.;
́
̌
̌
Teply, F.; Vyskoci
̌
l, S.; Saman, D. Tetrahedron Lett. 1999, 40, 1993.
́
̌
(b) Teply, F.; Stara,
́
I. G.; Stary, I.; Kollar
́
ovic,
S.; Fiedler, P. J. Org. Chem. 2003, 68, 5193. (c) Janca
Cocq, K.; Chocholousova, J. V.; Vacek, J.; Pohl, R.; Bednar
Fiedler, P.; Cisarova, I.; Stara, I. G.; Stary, I. Angew. Chem., Int. Ed. 2013,
52, 9970. (d) Buchta, M.; Rybac
Budes nsky, M.; Chocholousova,
Císaro I.; Bodwell, G. J.; Stary, I.; Stara,
21, 8910.
̌
A.; Saman, D.; Vyskoci
rik, A.; Rybac k, J.;
ova, L.;
̌
l,
́
́
̌
̌
̌
́ ̌
e
̌
́
́
́
̌
́
́
́
́
ek, J.; Janca
J. V.; Vacek, J.; Bednar
I. G. Chem. - Eur. J. 2015,
̌
rí
̌
k, A.; Kudale, A. A.;
̌
í
̌
́
̌
́
́
ova, L.;
́
̌
va,
́
́
́
(5) For iridium(I) catalysis, see: Shibata, T.; Uchiyama, T.; Yoshinami,
Y.; Takayasu, S.; Tsuchikama, K.; Endo, K. Chem. Commun. 2012, 48,
1311.
(6) For cobalt(I) catalysis, see: (a) Heller, B.; Hapke, M.; Fischer, C.;
Andronova, A.; Stary, I.; Stara,
́
I. G. J. Organomet. Chem. 2013, 723, 98.
k, A.; Saman, D.; Pohl, R.; Fiedler, P.; Bednarova, L.;
I. G. Chem. - Eur. J. 2016, 22, 14401.
́
̌
(b) Klívar, J.; Janca
Stary, I.; Stara,
̌
ri
̌
́
́
́
́
(7) For other recent examples of the enantioselective synthesis of
helicenes and helicene-like molecules, see: (a) Sako, M.; Takeuchi, Y.;
Tsujihara, T.; Kodera, J.; Kawano, T.; Takizawa, S.; Sasai, H. J. Am.
Chem. Soc. 2016, 138, 11481. (b) Tanaka, M.; Shibata, Y.; Nakamura, K.;
D
Org. Lett. XXXX, XXX, XXX−XXX