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Volumn , Issue 13, 2003, Pages 2047-2051

Further Application of an N-Ar Axially Chiral Mimetic-Type Ligand: Asymmetric Grignard Cross-Coupling Reaction

Author keywords

Asymmetric Kumada Corriu reaction; Chiral mimetics; Grignard cross coupling; N AR axis; Optically active ligand

Indexed keywords

LIGAND; N [2 (DIPHENYLPHOSPHANYL)NAPHTHALEN 1 YL] 2 (PIPERIDINYLMETHYL)PIPERIDINE; PIPERIDINE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242332785     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41485     Document Type: Article
Times cited : (27)

References (61)
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    • Grignard cross-coupling reaction is called the Kumada-Corriu reaction: (a) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374. (b) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
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    • Grignard cross-coupling reaction is called the Kumada-Corriu reaction: (a) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374. (b) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
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    • note
    • 2, gave less satisfactory results.
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    • note
    • The use of ligand 1i at ca.-20 °C afforded the coupling product with 25% yield and 80% ee.
  • 34
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    • note
    • 3): δ = 1.24 (d, J = 6.9 Hz, 3 H x 2), 2.88 (sept, J = 6.9 Hz, 1 H), 6.70 (d, J = 13.8 Hz, 1 H), 7.07 (d, J = 13.8 Hz, 1 H), 7.13-7.29 (m, 4 H).
  • 35
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    • note
    • The use of vinyl bromide and 1-propenyl bromide as substrates resulted in no reaction.
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    • note
    • The racemic and optically active carboxylic acid 7 were purchased from Aldrich Co., Ltd.
  • 37
    • 0242359591 scopus 로고    scopus 로고
    • note
    • 2 (9.3 mg, 0.036 mmol) and the ligand 1j (18.2 mg, 0.0369 mmol) in α,α,α-trifluorotoluene (2.10 mL) at 0 °C, and the solution was stirred at the same temperature for 30 min (CAUTION: stirring at 0 °C for 30 min for the favorable complexation of Pd and ligand 1j is needed.). To the solution was added (E)-β- bromostyrene (3a) (133 mg, 0.727 mmol) at -10 °C. The resulting solution was stirred for 6 h at -10 °C. After usual work-up, purification by silica gel column(hexane) afforded the coupling product 5a (105 mg, 69%, 72% ee) as a colorless oil.
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    • For other catalytic asymmetric Grignard cross-couplings, see: (a) Tamao, K.; Minato, A.; Miyake, N.; Matsuda, T.; Kiso, Y.; Kumada, M. Chem. Lett. 1975, 133. (b) Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumada, M. Tetrahedron Lett. 1977, 1389. (c) Hayashi, T.; Konishi, M.; Okamoto, Y.; Kabeta, K.; Kumada, M. J. Org. Chem. 1986, 51, 3772. (d) Iida, A.; Yamashita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2365. (e) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153. (f) Hayashi, T.; Hayashizaki, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 215. (g) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. (h) Kamikawa, T.; Hayashi, T. Tetrahedron 1999, 55, 3455. (i) Hölzer, B.; Hoffmann, R. W. Chem. Commun. 2003, 732.
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    • Cho, S.Y.1    Shibasaki, M.2
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    • Jin, M.-J.1    Kim, S.-H.2    Lee, S.-J.3    Kim, Y.-M.4
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    • 3)-ligands, see: (a) Mino, T.; Tanaka, Y.; Akita, K.; Sakamoto, M.; Fujita, T. Heterocycles 2003, 60, 9. (b) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769. (c) Jin, M.-J. ; Kim, S.-H.; Lee, S.-J.; Kim, Y.-M. Tetrahedron Lett. 2002, 43, 7409. (d) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (e) Mino, T.; Hata, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (f) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193. (g) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89. (h) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157. (i) Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073. (j) Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203; and references cited therein.
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    • Okuyama, Y.1    Nakano, H.2    Hongo, H.3
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    • 3)-ligands, see: (a) Mino, T.; Tanaka, Y.; Akita, K.; Sakamoto, M.; Fujita, T. Heterocycles 2003, 60, 9. (b) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769. (c) Jin, M.-J. ; Kim, S.-H.; Lee, S.-J.; Kim, Y.-M. Tetrahedron Lett. 2002, 43, 7409. (d) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (e) Mino, T.; Hata, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (f) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193. (g) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89. (h) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157. (i) Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073. (j) Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203; and references cited therein.
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    • Suzuki, Y.1    Abe, I.2    Hiroi, K.3
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    • 3)-ligands, see: (a) Mino, T.; Tanaka, Y.; Akita, K.; Sakamoto, M.; Fujita, T. Heterocycles 2003, 60, 9. (b) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769. (c) Jin, M.-J. ; Kim, S.-H.; Lee, S.-J.; Kim, Y.-M. Tetrahedron Lett. 2002, 43, 7409. (d) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (e) Mino, T.; Hata, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (f) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193. (g) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89. (h) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157. (i) Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073. (j) Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203; and references cited therein.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4157
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    • 3)-ligands, see: (a) Mino, T.; Tanaka, Y.; Akita, K.; Sakamoto, M.; Fujita, T. Heterocycles 2003, 60, 9. (b) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769. (c) Jin, M.-J. ; Kim, S.-H.; Lee, S.-J.; Kim, Y.-M. Tetrahedron Lett. 2002, 43, 7409. (d) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (e) Mino, T.; Hata, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (f) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193. (g) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89. (h) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157. (i) Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073. (j) Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203; and references cited therein.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1073
    • Bourghida, M.1    Widhalm, M.2
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    • and references cited therein
    • 3)-ligands, see: (a) Mino, T.; Tanaka, Y.; Akita, K.; Sakamoto, M.; Fujita, T. Heterocycles 2003, 60, 9. (b) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769. (c) Jin, M.-J. ; Kim, S.-H.; Lee, S.-J.; Kim, Y.-M. Tetrahedron Lett. 2002, 43, 7409. (d) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (e) Mino, T.; Hata, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (f) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193. (g) Suzuki, Y.; Abe, I.; Hiroi, K. Heterocycles 1999, 50, 89. (h) Cahill, J. P.; Cunneen, D.; Guiry, P. J. Tetrahedron: Asymmetry 1999, 10, 4157. (i) Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073. (j) Hattori, T.; Komuro, Y.; Hayashizaka, N.; Takahashi, H.; Miyano, S. Enantiomer 1997, 2, 203; and references cited therein.
    • (1997) Enantiomer , vol.2 , pp. 203
    • Hattori, T.1    Komuro, Y.2    Hayashizaka, N.3    Takahashi, H.4    Miyano, S.5
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    • During the completion of this manuscript, we became aware of a recent report by Mino, T. et al. of the Pd-catalyzed asymmetric allylic alkylation with the ligand 1m: Mino, T.; Tanaka, Y.; Sato, Y.; Saito, A.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2003, 44, 4677.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 4677
    • Mino, T.1    Tanaka, Y.2    Sato, Y.3    Saito, A.4    Sakamoto, M.5    Fujita, T.6


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