Preparation of germyl-substituted dizinciomethanes and their reactions with electrophiles

Synlett

Volumn , Issue 4, 2000, Pages 495-496

  Matsubara, Seijiro ^a   Yoshino, Hideaki ^a   Utimoto, Kiitiro ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Coupling; Germane; Olefination; Zinc

Indexed keywords

ALDEHYDE; BROMIDE; LEAD; METHANE; ORGANOHALOGEN DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034079758     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
2. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
3. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
4. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
5. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
6. Marek, I.; Normant, J.-F. Chem. Rev. 1996, 96, 3241; Matsubara, S. J. Synth. Org. Chem., 2000, 58, 108; Knochel, P.; Normant, J.-F. Tetrahedron Lett. 1986, 27, 4427 and 4431; Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457; Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B. J. J.; Schat, G.; Tinga, M. A. G. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
7. (a) Utimoto, K.; Toda, N.; Mizuno, T.; Kobata, M.; Matsubara, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2804.
8. (b) Matsubara, S.; Mizuno, T.; Otake, Y.; Kobara, M.; Utimoto, K.; Takai, K. Synlett 1998, 1369.
9. (c) Matsubara, S.; Otake, Y.; Hashimoto, Y.; Utimoto, K. Chem. Lett. 1999, 747.
10. (d) Matsubara, S.; Yamamoto, Y.; Utimoto, K. Synlett 1999, 1411
11. (a) Matsubara, S.; Otake, Y.; Morikawa, T.; Utimoto, K. Synlett 1998, 1315.
12. (b) Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett., 1987, 28, 1443;
13. Takai, K.; Hikasa, S.; Ichiguchi, T.; Sumino, N. Synlett, 1999, 1769.
14. (c) Hodgson, D. M.; Comina, P. J. Synlett, 1994, 663.
15. For example; Ingold, K. U.; Lusztyk, J.; Sciano, J. C. J. Am. Chem. Soc., 1984, 106, 343; Nakamura, T.; Yokoyama, Y.; Mochida, K. Synlett, 1997, 907; Ulrich, I.; Curran, D. P. J. Org. Chem. 63, 4711; Nakanoo, T.; Enokido, T.; Noda, S.; Aihara, N.; Kossugi, M.; Migita, T. J. Organomet. Chem. 1998, 553, 493; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett, 1999, 1415.
16. For example; Ingold, K. U.; Lusztyk, J.; Sciano, J. C. J. Am. Chem. Soc., 1984, 106, 343; Nakamura, T.; Yokoyama, Y.; Mochida, K. Synlett, 1997, 907; Ulrich, I.; Curran, D. P. J. Org. Chem. 63, 4711; Nakanoo, T.; Enokido, T.; Noda, S.; Aihara, N.; Kossugi, M.; Migita, T. J. Organomet. Chem. 1998, 553, 493; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett, 1999, 1415.
17. For example; Ingold, K. U.; Lusztyk, J.; Sciano, J. C. J. Am. Chem. Soc., 1984, 106, 343; Nakamura, T.; Yokoyama, Y.; Mochida, K. Synlett, 1997, 907; Ulrich, I.; Curran, D. P. J. Org. Chem. 63, 4711; Nakanoo, T.; Enokido, T.; Noda, S.; Aihara, N.; Kossugi, M.; Migita, T. J. Organomet. Chem. 1998, 553, 493; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett, 1999, 1415.
18. For example; Ingold, K. U.; Lusztyk, J.; Sciano, J. C. J. Am. Chem. Soc., 1984, 106, 343; Nakamura, T.; Yokoyama, Y.; Mochida, K. Synlett, 1997, 907; Ulrich, I.; Curran, D. P. J. Org. Chem. 63, 4711; Nakanoo, T.; Enokido, T.; Noda, S.; Aihara, N.; Kossugi, M.; Migita, T. J. Organomet. Chem. 1998, 553, 493; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett, 1999, 1415.
19. For example; Ingold, K. U.; Lusztyk, J.; Sciano, J. C. J. Am. Chem. Soc., 1984, 106, 343; Nakamura, T.; Yokoyama, Y.; Mochida, K. Synlett, 1997, 907; Ulrich, I.; Curran, D. P. J. Org. Chem. 63, 4711; Nakanoo, T.; Enokido, T.; Noda, S.; Aihara, N.; Kossugi, M.; Migita, T. J. Organomet. Chem. 1998, 553, 493; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett, 1999, 1415.
20. 3GeCl and dibromomethane with lithium diisopropylamide at -78 °C.
21. 6) δ 0.97 (bs, 1H), 0.8-1.0 (m, 6H), 1.0-1.2 (m, 9H). The yield was calculated by using 2,2,3,3-tetramethylbutane as an internal standard.
22. 3) δ 7.05-7.15 (m, 5H), 6.41 (dt, J = 6.0, 12.1 Hz, 0.18H, Z isomer), 6.00 (dt, J = 6.0, 18.9 Hz, 0.82H, E isomer), 5.70 (d, J = 18.1 Hz, 0.82H, E isomer), 5.61 (d, J = 12.1 Hz, 0.18H, Z isomer), 2.73 (t, J = 7.5 Hz, 2H), 2.41 (t, 6.0, 7.5 Hz, 2H), 1.05 (t, J = 7.5 Hz, 9H), 0.82 (q, J = 7.5 Hz, 6H).
23. Knochel, P.; Singer, R. D. Chem. Rev., 1993, 93, 2117; Knochel, P. Synlett 1995, 393.
24. Knochel, P.; Singer, R. D. Chem. Rev., 1993, 93, 2117; Knochel, P. Synlett 1995, 393.
25. 3) δ 7.05-7.4 (m, 5H), 6.39 (d, J = 16.5 Hz, 1H), 6.26 (dt, J = 6.6, 16.5Hz, 1H), 5.19 (dt, J = 6.6, 7.8, 1H), 4.73 (dd, J = 2.1, 6.6, 2H), 2.42 (t, J = 6.6 Hz, 2H), 1.89 (m, 1H), 1.08 (t, J = 7.5Hz, 9H), 0.92 (q, J = 7.5Hz, 6H).
26. Pillot, J. P.; Dunoguès, J., Calas, R. Bull. Chim. Soc. Fr. 1975, 2143.