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Volumn 7, Issue 2, 2005, Pages 307-310

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMINE; BORON DERIVATIVE; IMINE; LIGAND; RHODIUM;

EID: 13444262183     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0476063     Document Type: Article
Times cited : (173)

References (29)
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    • Other reports on the catalytic enantioselective arylation of arylimines giving enantiomerically enriched diarylmethylamines: (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692. (c) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128. (d) Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
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    • Other reports on the catalytic enantioselective arylation of arylimines giving enantiomerically enriched diarylmethylamines: (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692. (c) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128. (d) Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3692
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  • 9
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    • Other reports on the catalytic enantioselective arylation of arylimines giving enantiomerically enriched diarylmethylamines: (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692. (c) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128. (d) Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8128
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  • 10
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    • Other reports on the catalytic enantioselective arylation of arylimines giving enantiomerically enriched diarylmethylamines: (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692. (c) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128. (d) Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6125
    • Hayashi, T.1    Kawai, M.2    Tokunaga, N.3
  • 11
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    • Rhodium-catalyzed arylation of N-tosylimines with arylboron reagents was first reported by Miyaura: (a) Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31. (b) Ueda, M.; Saito, A.; Miyaura, N. Synlett 2000, 1637.
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    • Rhodium-catalyzed arylation of N-tosylimines with arylboron reagents was first reported by Miyaura: (a) Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31. (b) Ueda, M.; Saito, A.; Miyaura, N. Synlett 2000, 1637.
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    • note
    • 2/HMPA: see ref 7d.
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    • note
    • 3).
  • 20
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    • note
    • 3): δ 32.94, 34.61, 41.47, 72.68 (d, J = 11.4 Hz), 86.22 (d, J = 14.5 Hz), 126.54, 126.64, 127.77, 144.77 (d, J = 2.1 Hz).
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    • Prepared from aromatic aldehydes and 4-nitrobenzenesulfonamide in the presence of tetraethoxysilane: Love, B. E.; Raje, P. S.; Williams II. T. C. Synlett 1994, 493.
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    • note
    • Low efficiency of the chiral phosphorus ligands has been also observed in the arylation of N-tosylimines: see ref 6.
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    • For reviews: (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (c) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns. N. Angew. Chem., Int. Ed. 2001, 40, 3284.
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    • Hayashi, T.1    Yamasaki, K.2
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    • For reviews: (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (c) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns. N. Angew. Chem., Int. Ed. 2001, 40, 3284.
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    • Fagnou, K.1    Lautens, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.