H. Hara et al. / Tetrahedron 65 (2009) 5093–5101
5101
26.8, 26.0; HRMS (ESI) calcd for C16H20O4Na [MþNa]þ 299.1254,
Synlett 2008, 755; For a review of neutral iridium(I)/diphosphine complex-
catalyzed enantioselective [2þ2þ2] cycloadditions, see: Ref. 1c.
found 299.1254.
4. Although palladium-catalyzed [2þ2þ2] cycloadditions of dimethyl acetylene-
dicarboxylate with vinyl ethers and esters were reported, the reactions re-
quired a large excess of the vinyl compounds (100 equiv) and a long reaction
time (3–5 days), see: Stephan, C.; Munz, C.; Dieck, H. T. J. Organomet. Chem.
1993, 452, 223.
4.4.17. Biphenyl-2,3-dicarboxylic acid dimethyl ester (15ahj)
Pale yellow solid; mp 92.1–93.8 ꢀC; IR (KBr) 2953, 1963, 1911,
1719, 1587, 1497, 1436 cmꢁ1
;
1H NMR (CDCl3)
d
8.00 (d, J¼6.9 Hz,
1H), 7.58–7.48 (m, 2H), 7.45–7.41 (m, 5H), 3.91 (s, 3H), 3.67 (s, 3H);
13C NMR (CDCl3)
169.2, 166.2, 140.6, 139.2, 134.7, 134.2, 129.1,
5. For the use of ethyl vinyl ether as a synthetic equivalent of acetylene in
a DABCO-catalyzed microwave-assisted Diels–Alder–elimination reaction se-
quence, see: Kranjc, K.; Koevar, M. Synlett 2008, 2613.
6. For our accounts, see: (a) Tanaka, K. Synlett 2007, 1977; (b) Tanaka, K.; Nishida,
G.; Suda, T. J. Synth. Org. Chem. Jpn. 2007, 65, 862.
7. For a review of rhodium-catalyzed cyclotrimerization reactions, see: Fujiwara,
M.; Ojima, I. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.;
Wiley-VCH: Weinheim, 2005; p 129.
d
128.8, 128.6, 128.3, 128.1, 127.9, 52.6, 52.3; HRMS (ESI) calcd for
C16H14O4Na [MþNa]þ 293.0784, found 293.0784.
4.4.18. 3-(Trimethylsilanyl)phthalic acid dimethyl ester (15aij)
8. (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697; (b) Tanaka, K.; Nishida, G.;
Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510; (c) Tanaka, K.;
Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem.dEur. J. 2005, 11, 1145; (d)
Tanaka, K.; Nishida, G.; Ogino, M.; Hirano, M.; Noguchi, K. Org. Lett. 2005, 7,
3119; (e) Tanaka, K.; Sagae, H.; Toyoda, K.; Noguchi, K. Eur. J. Org. Chem. 2006,
3575; (f) Nishida, G.; Suzuki, N.; Noguchi, K.; Tanaka, K. Org. Lett. 2006, 8, 3489;
(g) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586; (h)
Tanaka, K.; Suda, T.; Noguchi, K.; Hirano, M. J. Org. Chem. 2007, 72, 2243; (i)
Tanaka, K.; Sagae, H.; Toyoda, K.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007,
129, 1522; (j) Tanaka, K.; Osaka, T.; Noguchi, K.; Hirano, M. Org. Lett. 2007, 9,
1307; (k) Tanaka, K.; Hara, H.; Nishida, G.; Hirano, M. Org. Lett. 2007, 9, 1907; (l)
Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2007, 46,
3951; (m) Tanaka, K.; Kamisawa, A.; Suda, T.; Noguchi, K.; Hirano, M. J. Am.
Chem. Soc. 2007, 129, 12078; (n) Tanaka, K.; Sagae, H.; Toyoda, K.; Hirano, M.
Tetrahedron 2008, 64, 831; (o) Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K.
Angew. Chem., Int. Ed. 2008, 47, 3410; (p) Nishida, G.; Ogaki, S.; Yusa, Y.;
Yokozawa, T.; Noguchi, K.; Tanaka, K. Org. Lett. 2008, 10, 2849; (q) Suda, T.;
Noguchi, K.; Hirano, M.; Tanaka, K. Chem.dEur. J. 2008, 14, 6593.
9. (a) Tsuchikama, K.; Kuwata, Y.; Shibata, T. J. Am. Chem. Soc. 2006, 128, 13686; (b)
Tanaka, K.; Nishida, G.; Sagae, H.; Hirano, M. Synlett 2007, 1426; (c) Shibata, T.;
Kawachi, A.; Ogawa, M.; Kuwata, Y.; Tsuchikama, K.; Endo, K. Tetrahedron 2007,
63, 12853; (d) Shibata, Y.; Noguchi, K.; Hirano, M.; Tanaka, K. Org. Lett. 2008, 10,
2825; (e) Tanaka, K.; Takahashi, M.; Imase, H.; Osaka, T.; Noguchi, K.; Hirano, M.
Tetrahedron 2008, 64, 6289.
Colorless oil; IR (neat) 2952, 2900, 1732, 1573, 1441, 1282, 1107,
961, 842, 764 cmꢁ1; 1H NMR (CDCl3)
d
7.93 (d, J¼7.8 Hz, 1H), 7.57 (d,
J¼7.8 Hz, 1H), 7.47 (t, J¼7.8 Hz, 1H), 3.91 (s, 3H), 3.90 (s, 3H), 0.31 (s,
9H); 13C NMR (CDCl3)
d 170.5, 166.9, 140.0, 138.8, 138.3, 130.2, 128.6,
128.4, 52.4, 52.3, ꢁ0.5; HRMS (EI) calcd for C12H15O4Si [MꢁMe]þ
251.0739, found 251.0701.
Acknowledgements
This work was partly supported by a Grant-in-Aid for Scientific
Research (Nos. 20675002, 19350046, and 19028015) from JSPS and
MEXT, Japan. We are grateful to Takasago International Corporation
for the gift of Segphos and H8-BINAP, and Umicore for generous
supports in supply of rhodium complexes.
References and notes
10. The preliminary communication of this work has been reported, see: Hara, H.;
Hirano, M.; Tanaka, K. Org. Lett. 2008, 10, 2537.
1. For reviews of transition-metal-catalyzed [2þ2þ2] cycloadditions, see: (a) Ta-
´
11. Although the reaction of 1a with vinyl acetate (2j) was also examined, 3aa was
obtained in lower yield (47%) than that with 2a.
12. For cationic rhodium(I)/BINAP complex-catalyzed [2þ2þ2] cycloadditions of
diynes with alkynyl ethers en route to aryl ethers, see: Clayden, J.; Moran, W. J.
Org. Biomol. Chem. 2007, 5, 1028.
Saa, C. Synlett 2008, 2571; (c) Shibata, T.; Tsuchikama, K. Org. Biomol. Chem.
2008, 1317; (d) Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085; (e) Agenet,
N.; Buisine, O.; Slowinski, F.; Gandon, V.; Aubert, C.; Malacria, M. In Organic
Reactions; RajanBabu, T. V., Ed.; John Wiley & Sons: Hoboken, 2007; Vol. 68, p 1;
(f) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307; (g) Gandon, V.;
Aubert, C.; Malacria, M. Chem. Commun. 2006, 2209; (h) Kotha, S.; Brahmachary,
E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741; (i) Gandon, V.; Aubert, C.; Malacria, M.
Curr. Org. Chem. 2005, 9, 1699; (j) Yamamoto, Y. Curr. Org. Chem. 2005, 9, 503;
(k) Varela, J.; Saa´, C. Chem. Rev. 2003, 103, 3787; (l) Malacria, M.; Aubert, C.;
Renaud, J. L. In Science of Synthesis: Houben-Weyl Methods for Molecular Trans-
formations; Lautens, M., Trost, B. M., Eds.; Georg Thieme: New York, NY, 2001;
Vol. 1, p 439; (m) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901; (n)
Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone,
F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 741;
(o) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374; (p) Schore,
N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Perga-
mon: Oxford, 1991; Vol. 5, p 1129; (q) Vollhardt, K. P. C. Angew. Chem., Int. Ed.
Engl. 1984, 23, 539.
2. For selected recent examples, see: (a) Heller, B.; Gutnov, A.; Fischer, C.; Drexler,
H.-J.; Spannenberg, A.; Redkin, D.; Sundermann, C.; Sundermann, B.
Chem.dEur. J. 2007, 13, 1117; (b) Ramana, C. V.; Salian, S. R.; Gonnade, R. G.
Eur. J. Org. Chem. 2007, 5483; (c) Young, D. D.; Senaiar, R. S.; Deiters, A. Chem.dEur.
J. 2006, 12, 5563; (d) Yamamoto, Y.; Hashimoto, T.; Hattori, K.; Kikuchi, M.;
Nishiyama, H. Org. Lett. 2006, 8, 3565; (e) Yamamoto, Y.; Kinpara, K.;
Saigoku, T.; Nishiyama, H.; Itoh, K. Org. Biomol. Chem. 2004, 2, 1287;
(f) Yamamoto, Y.; Hata, K.; Arakawa, T.; Itoh, K. Chem. Commun. 2003, 1290; (g)
Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143;
(h) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281; (i) Witulski, B.;
Zimmermann, A. Synlett 2002, 1855; (j) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem.
Commun. 2000, 549; (k) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38,
2426; (l) Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231; (m)
McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc.1995,117, 6605; (n)
Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
13. Tanaka, K.; Suzuki, N.; Nishida, G. Eur. J. Org. Chem. 2006, 3917.
14. For examples of transition-metal-catalyzed intermolecular three-component
cocyclotrimerizations, see: (a) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999,
121, 2722; (b) Mori, N.; Ikeda, S.; Odashima, K. Chem. Commun. 2001, 181; (c)
Chouraqui, G.; Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 1519; (d)
Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712;
(e) Ura, Y.; Sato, Y.; Tsujita, H.; Kondo, T.; Imachi, M.; Mitsudo, T. J. Mol. Catal. A
2005, 239, 166; (f) Deng, L.; Giessert, A. J.; Gerlitz, O. O.; Dai, X.; Diver, S. T.;
Davies, H. M. L. J. Am. Chem. Soc. 2005, 127, 1342; (g) Yamamoto, Y.; Ishii, J.;
Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 9625; (h) Komagawa, S.;
Saito, S. Angew. Chem., Int. Ed. 2006, 45, 2446.
15. For examples of intermolecular three-component cocyclotrimerizations using
stoichiometric transition-metal complexes, see: (a) Wakatsuki, Y.; Aoki, K.;
Yamazaki, H. J. Am. Chem. Soc. 1979, 101, 1123; (b) Takahashi, T.; Kotora, M.; Xi, Z.
J. Chem. Soc., Chem. Commun. 1995, 361; (c) Takahashi, T.; Xi, Z.; Yamazaki, A.;
Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672; (d) Takahashi,
T.; Tsai, F.-Y.; Li, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093;
(e) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925; (f) Takahashi,
T.; Tsai, F.-Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M.
J. Am. Chem. Soc. 2002, 124, 5059; (g) Tanaka, R.; Nakano, Y.; Suzuki, D.; Urabe,
H.; Sato, F. J. Am. Chem. Soc. 2002, 124, 9682.
16. Atkinson, R. S.; Grimshir, M. J. J. Chem. Soc., Perkin Trans. 1 1986, 1215.
17. Nishida, H.; Mori, M. J. Org. Chem. 1998, 63, 8606.
18. Kudoh, T.; Mori, T.; Shirahama, M.; Yamada, M.; Ishikawa, T.; Saito, S.;
Kobayashi, H. J. Am. Chem. Soc. 2007, 129, 4939.
19. Matano, Y.; Miyajima, T.; Nakabuchi, T.; Matsutani, Y.; Imahori, H. J. Org. Chem.
2006, 71, 5792.
20. James, W. M.; Xiang, W.; Ross, A. W. Org. Lett. 2001, 3, 385.
21. Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K.
Chem.dEur. J. 2003, 2469.
22. Grubbs, R. H.; Pancoast, T. A. J. Am. Chem. Soc. 1977, 99, 2382.
23. Yanagita, M.; Futaki, R. J. Org. Chem. 1956, 21, 949.
24. Park, I. S.;Kwon, M. S.;Kang, K. Y.; Lee, J. S.;Park, J. Adv. Synth. Catal. 2007, 349, 209.
25. Alder, K.; Gunzl-Schumacher, M. Chem. Ber. 1959, 92, 822.
3. (a) Kezuka, S.; Tanaka, S.; Ohe, T.; Nakaya, Y.; Takeuchi, R. J. Org. Chem. 2006, 71,
543; For their works on neutral iridium(I)/diphosphine complex-catalyzed
[2þ2þ2] cycloadditions, see: (b) Takeuchi, R.; Tanaka, S.; Nakaya, Y. Tetrahedron
Lett. 2001, 42, 2991; (c) Takeuchi, R.; Nakaya, Y. Org. Lett. 2003, 5, 3659; (d)
Kezuka, S.; Okado, T.; Niou, E.; Takeuchi, R. Org. Lett. 2005, 7, 1711; (e) Onodera,
G.; Matsuzawa, M.; Aizawa, T.; Kitahara, T.; Shimizu, Y.; Kezuka, S.; Takeuchi, R.