Palladium-catalyzed asymmetric synthesis of axially chiral (allenylmethyl)silanes and chirality transfer to stereogenic carbon centers in SE′ reactions

Organic Letters

Volumn 5, Issue 2, 2003, Pages 217-219

  Ogasawara, Masamichi ^a,b   Ueyama, Kazuhito ^a   Nagano, Takashi ^a   Mizuhata, Yoshiyuki ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(3 BROMOPENTA 2,4 DIENYL)TRIMETHYLSILANE; CHLORINE DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; GEOMETRY; STEREOCHEMISTRY;

EID: 0038517213     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027291w     Document Type: Article

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27. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
28. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
29. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
30. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
31. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
32. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
33. For preparation of (allenylmethyl)silanes, see: (a) Pornet, J.; Kolani, N. Tetrahedron Lett. 1981, 22, 3609. (b) Nativi, C.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987, 28, 2751. (c) Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723. (d) Creary, X.; Jiang, Z.; Butchko, M.; McLean, K. Tetrahedron Lett. 1996, 37, 579. (e) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 8, 11377. (f) Lahrech, M.; Hacini, S.; Parrain, J.-L.; Santelli, M. Tetrahedron Lett. 1997, 38, 3395. (g) Maruyama, Y.; Yoshiuchi, K.; Ozawa, F. J. Organomet. Chem. 1999, 64, 8582. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. See also ref 6a.
34. For application of (allenylmethyl)silanes to other organic transformations, see, (a) Trost, B. M.; Urabe, H. J. Am. Chem. Soc. 1990, 112, 4982. (b) Colvin, E. W.; Monteith, M. J. Chem. Soc., Chem. Commun. 1990, 1230. (c) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (d) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. (e) Hojo, M.; Murakami, C.; Aihara, H.; Tomita, K.; Miura, K.; Hosomi, A. J. Organomet. Chem. 1995, 499, 155. (f) Nishiyama, T.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 43. (g) Hojo, M.; Murakami, C.; Nakamura, S.; Hosomi, A. Chem. Lett. 1998, 331.
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36. For application of (allenylmethyl)silanes to other organic transformations, see, (a) Trost, B. M.; Urabe, H. J. Am. Chem. Soc. 1990, 112, 4982. (b) Colvin, E. W.; Monteith, M. J. Chem. Soc., Chem. Commun. 1990, 1230. (c) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (d) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. (e) Hojo, M.; Murakami, C.; Aihara, H.; Tomita, K.; Miura, K.; Hosomi, A. J. Organomet. Chem. 1995, 499, 155. (f) Nishiyama, T.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 43. (g) Hojo, M.; Murakami, C.; Nakamura, S.; Hosomi, A. Chem. Lett. 1998, 331.
37. For application of (allenylmethyl)silanes to other organic transformations, see, (a) Trost, B. M.; Urabe, H. J. Am. Chem. Soc. 1990, 112, 4982. (b) Colvin, E. W.; Monteith, M. J. Chem. Soc., Chem. Commun. 1990, 1230. (c) Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. (d) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. (e) Hojo, M.; Murakami, C.; Aihara, H.; Tomita, K.; Miura, K.; Hosomi, A. J. Organomet. Chem. 1995, 499, 155. (f) Nishiyama, T.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Tetrahedron Lett. 1998, 39, 43. (g) Hojo, M.; Murakami, C.; Nakamura, S.; Hosomi, A. Chem. Lett. 1998, 331.
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