J. Oyamada et al. / Journal of Organometallic Chemistry 694 (2009) 3626–3632
3631
(d, J = 12.0 Hz, 1H, vinyl), 9.43 (brs, 1H, CO2H); 13C NMR (75 MHz,
CDCl3) 30.93, 31.10, 34.15, 35.36, 118.67, 125.11, 125.54,
Acknowledgements
d
128.41, 134.11, 144.31, 147.84, 150.24, 171.65. Anal. Calc. for
C17H24O2: C, 78.42; H, 9.29. Found: C, 78.35; H, 9.19%.
This work was supported by a Grant-in-Aid for Scientific Re-
search on Priority Areas ‘‘Advanced Molecular Transformations of
Carbon Resources” from the Ministry of Education, Culture, Sports,
Science and Technology, Japan, and by management expenses
grants for national university corporations. J.O. thanks JSPS
Research Fellowships for Young Scientists.
4.13. Ethyl (2Z)-3-(2,5-dimethylphenyl)propenoate (4a) [5b]
Colorless liquid; 1H NMR (300 MHz, CDCl3) d 1.14 (t, J = 7.1 Hz,
3H, CH3), 2.23 (s, 3H, aryl-CH3), 2.29 (s, 3H, aryl-CH3), 4.09 (q,
J = 7.1 Hz, 2H, OCH2), 6.00 (d, J = 12.0 Hz, 1H, vinyl), 6.98–7.08
(m, 2H, aryl), 7.08 (d, J = 12.0 Hz, 1H, vinyl), 7.11 (s, 1H, aryl); 13C
References
[1] (a) F. Kakiuchi, S. Murai, Top. Organometallic Chem. 3 (1999) 47;
(b) A.E. Shilov, G.B. Shul’pin, Chem. Rev. 97 (1997) 2879;
(c) G. Dyker, Angew. Chem., Int. Ed. Engl. 38 (1999) 1698;
(d) Y. Guari, S. Sabo-Etienne, B. Chaudret, Eur. J. Inorg. Chem. (1999) 1047;
(e) R.H. Crabtree, J. Chem. Soc., Dalton Trans. (2001) 2437;
(f) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 34 (2001) 633;
(g) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 102 (2002) 1731;
(h) F. Kakiuchi, S. Murai, Acc. Chem. Res. 35 (2002) 826;
(i) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 345 (2003) 1077.
[2] (a) For recent reviews, see: C. Nevado, A.M. Echavarren, Synthesis (2005) 167;
(b) T. Kitamura, Eur. J. Org. Chem. (2009) 1111.
[3] (a) P. Hong, B.-R. Cho, H. Yamazaki, Chem. Lett. 8 (1979) 339;
(b) P. Hong, B.-R. Cho, H. Yamazaki, Chem. Lett. 9 (1980) 507;
(c) H. Yamazaki, P. Hong, J. Mol. Catal. 21 (1983) 133.
[4] (a) B.M. Trost, F.D. Toste, J. Am. Chem. Soc. 118 (1996) 6305;
(b) B.M. Trost, F.D. Toste, K. Greenman, J. Am. Chem. Soc. 125 (2003) 4518.
[5] (a) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 287
(2000) 1992;
NMR (75 MHz, CDCl3)
d 13.94, 19.33, 20.88, 60.06, 120.99,
129.09, 129.26, 129.53, 132.61, 134.46, 134.87, 142.86, 166.09.
4.14. Ethyl (2Z)-3-(2,4,6-trimethylphenyl)propenoate (4b) [5b]
Colorless liquid; 1H NMR (300 MHz, CDCl3) d 1.10 (t, J = 7.1 Hz,
3H, CH3), 2.16 (s, 6H, aryl-CH3), 2.27 (s, 3H, aryl-CH3), 4.03 (q,
J = 7.1 Hz, 2H, OCH2), 6.11 (d, J = 12.0 Hz, 1H, vinyl), 6.84 (s, 2H,
aryl), 7.02 (d, J = 12.0 Hz, 1H, vinyl); 13C NMR (75 MHz, CDCl3) d
13.94, 20.11, 21.01, 59.92, 122.77, 127.78, 132.77, 134.44, 136.65,
144.13, 165.47.
4.15. Ethyl (2Z)-3-(pentamethylphenyl)propenoate (4c) [5b]
(b) C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am.
Chem. Soc. 122 (2000) 7252;
Colorless crystals; m.p. 72–74 °C; 1H NMR (300 MHz, CDCl3) d
1.10 (t, J = 7.1 Hz, 3H, CH3), 2.14 (s, 6H, aryl-CH3), 2.20 (s, 6H,
aryl-CH3), 2.22 (s, 3H, aryl-CH3), 4.01 (q, J = 7.1 Hz, 2H, OCH2),
6.13 (d, J = 12.0 Hz, 1H, vinyl), 7.12 (d, J = 12.0 Hz, 1H, vinyl); 13C
NMR (75 MHz, CDCl3) d 13.96, 16.36, 16.74, 17.59, 59.78, 122.13,
129.76, 131.89, 133.23, 133.95, 146.46, 165.42.
(c) C. Jia, D. Piao, T. Kitamura, Y. Fujiwara, J. Org. Chem. 65 (2000) 7516;
(d) W. Lu, C. Jia, T. Kitamura, Y. Fujiwara, Org. Lett. 2 (2000) 2927;
(e) J. Oyamada, W. Lu, C. Jia, T. Kitamura, Y. Fujiwara, Chem. Lett. 31 (2002) 20;
(f) J. Oyamada, C. Jia, Y. Fujiwara, T. Kitamura, Chem. Lett. 31 (2002) 380;
(g) T. Kitamura, K. Yamamoto, J. Oyamada, C. Jia, Y. Fujiwara, Bull. Chem. Soc.
Jpn. 76 (2003) 1889;
(h) M. Kotani, K. Yamamoto, J. Oyamada, Y. Fujiwara, T. Kitamura, Synthesis
(2004) 1466.
[6] J.A. Tunge, N.L. Foresee, Organometallics 24 (2005) 6440.
[7] M.S. Viciu, E.D. Stevens, J.L. Petersen, S.P. Nolan, Organometallics 23 (2004)
3752.
[8] (a) N. Tsukada, T. Mitsuboshi, H. Setoguchi, Y. Inoue, J. Am. Chem. Soc. 125
(2003) 12102;
4.16. Ethyl (2Z)-3-(3-hydroxy-2,4,6-trimethylphenyl)propenoate (4d)
[5b]
(b) N. Tsukada, K. Murata, Y. Inoue, Tetrahedron Lett. 46 (2005) 7515.
[9] M.T. Reetz, K. Sommer, Eur. J. Org. Chem. (2003) 3485.
[10] (a) Z. Shi, C. He, J. Org. Chem. 69 (2004) 3669;
(b) Z. Li, Z. Shi, C. He, J. Organomet. Chem. 690 (2005) 5049.
[11] (a) T. Tsuchimoto, T. Maeda, E. Shirakawa, Y. Kawakami, Chem. Commun.
(2000) 1573;
(b) T. Tsuchimoto, K. Hatanaka, E. Shirakawa, Y. Kawakami, Chem. Commun.
(2003) 2454.
[12] C.E. Song, D. Jung, S.Y. Choung, E.J. Roh, S. Lee, Angew. Chem., Int. Ed. 43 (2004)
6183.
Colorless crystals; m.p. 59–60 °C (hexane); 1H NMR (300 MHz,
CDCl3) d 1.11 (t, J = 7.1 Hz, 3H, CH3), 2.10 (s, 6H, aryl-CH3), 2.20
(s, 3H, aryl-CH3), 4.03 (q, J = 7.1 Hz, 2H, OCH2), 4.49 (s, 1H, OH),
6.13 (d, J = 12.0 Hz, 1H, vinyl), 6.80 (s, 1H, aryl), 7.00 (d,
J = 12.0 Hz, 1H, vinyl); 13C NMR (75 MHz, CDCl3) d 12.97, 13.96,
15.85, 19.54, 59.97, 120.18, 121.86, 122.86, 126.17, 129.15,
134.31, 143.94, 149.77, 165.39.
[13] Y. Nakao, K.S. Kanyiva, S. Oda, T. Hiyama, J. Am. Chem. Soc. 128 (2006) 8146.
[14] (a) G. Halbritter, F. Knoch, A. Wolski, H. Kisch, Angew. Chem., Int. Ed. Engl. 33
(1994) 1603;
4.17. Ethyl (2Z)-3-{3-[(1Z)-2-ethoxycarbonylethenyl]-2,4,6-
trimethylphenyl}propenoate (5a) [5b]
(b) U.R. Aulwurm, J.U. Melchinger, H. Kisch, Organometallics 14 (1995) 3385;
(c) U. Dürr, H. Kisch, Synlett (1997) 1335.
[15] (a) F. Kakiuchi, Y. Yamamoto, N. Chatani, S. Murai, Chem. Lett. 24 (1995)
681;
(b) F. Kakiuchi, T. Sato, T. Tsujimoto, M. Yamauchi, N. Chatani, S. Murai, Chem.
Lett. 27 (1998) 1053.
[16] P.W.R. Harris, C.E.F. Rickard, P.D. Woodgate, J. Organomet. Chem. 589 (1999)
168.
[17] Y.-G. Lim, K.-H. Lee, B.T. Koo, J.-B. Kang, Tetrahedron Lett. 42 (2001) 7609.
[18] T. Satoh, Y. Nishinaka, M. Miura, M. Nomura, Chem. Lett. 28 (1999) 615.
[19] N. Chatani, H. Inoue, T. Ikeda, S. Murai, J. Org. Chem. 65 (2000) 4913.
[20] H. Inoue, N. Chatani, S. Murai, J. Org. Chem. 67 (2002) 1414.
[21] (a) A. Fürstner, V. Mamane, J. Org. Chem. 67 (2002) 6264;
(b) V. Mamame, P. Hannen, A. Fürstner, Chem. Eur. J. 10 (2004) 4556.
[22] (a) S.J. Pastine, S.W. Youn, D. Sames, Org. Lett. 5 (2003) 1055;
(b) S.J. Pastine, S.W. Youn, D. Sames, Tetrahedron 59 (2003) 8859.
[23] M. Nishizawa, H. Takao, V.K. Yadav, H. Imagawa, T. Sugihara, Org. Lett. 5 (2003)
4563.
Light yellow oil; 1H NMR (300 MHz, CDCl3) d 1.12 (t, J = 7.1 Hz,
6H, CH3), 2.05 (s, 3H, aryl-CH3), 2.15 (s, 6H, aryl-CH3), 4.03 (q,
J = 7.1 Hz, 4H, OCH2), 6.12 (d, J = 11.7 Hz, 2H, vinyl), 6.88 (s, 1H,
aryl), 7.04 (d, J = 11.7 Hz, 2H, vinyl); 13C NMR (75 MHz, CDCl3) d
13.98, 17.66, 20.17, 59.90, 122.68, 128.36, 130.97, 132.98, 133.46,
144.40, 165.38.
4.18. Ethyl (2Z)-3-{5-[(1Z)-2-ethoxycarbonylethenyl]-3-hydroxy-
2,4,6-trimethylphenyl}propenoate (5b) [25b]
Colorless crystals; m.p. 109–112 °C; 1H NMR (300 MHz, CDCl3) d
1.12 (t, J = 7.1 Hz, 6H, CH3), 1.99 (s, 3H, aryl-CH3), 2.10 (s, 6H, aryl-
CH3), 4.03 (q, J = 7.1 Hz, 4H, OCH2), 4.53 (s, 1H, OH), 6.14 (d,
J = 12.0 Hz, 2H, vinyl), 7.02 (d, J = 12.0 Hz, 2H, vinyl); 13C NMR
(75 MHz, CDCl3) d 13.20, 13.98, 17.33, 59.95, 119.42, 122.87 (two
peaks overlapped), 133.85, 144.24, 149.44, 165.33; MS (EI, m/z)
332 (M+).
[24] (a) B. Matrín-Matute, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem.
Soc. 125 (2003) 5757;
(b) C. Nieto-Oberhuber, M.P. Muñoz, E. Buñuel, C. Nevado, D.J. Cárdenas, A.M.
Echavarren, Angew. Chem., Int. Ed. 43 (2004) 2402.
[25] (a) J. Oyamada, T. Kitamura, Tetrahedron Lett. 46 (2005) 3823;
(b) J. Oyamada, T. Kitamura, Tetrahedron 63 (2007) 12754.
[26] For a preliminary report, see: J. Oyamada, T. Kitamura, Chem. Lett. 34 (2005)
1430.