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Volumn 5, Issue 26, 2003, Pages 5059-5062

Phenylenebis(ethynyl)-Tethered Bis-BINOL Ligands for Enantioselective Catalyst Based on Dimeric Ti(IV) Aggregate

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIS 1,1' BI 2 NAPHTHOL; DIETHYLZINC; DIMER; NAPHTHOL DERIVATIVE; OXIDE; PHENYL GROUP; TITANIUM DERIVATIVE; TITANIUM TETRAISOPROPOXIDE; UNCLASSIFIED DRUG;

EID: 0347916938     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0360546     Document Type: Article
Times cited : (18)

References (33)
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    • and references therein
    • For structurally related bis-BINOLs and their use as ligands for chiral catalysts, see: (a) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. (b) Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161. (c) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (d) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712. (e) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169 and references therein, (f) Sekiguti, T.; lizuka, Y. ; Takizawa, S.; Jayaprakash, D.; Arai, T.; Sasai, H. Org. Lett. 2003, 5, 2647.
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    • For structurally related bis-BINOLs and their use as ligands for chiral catalysts, see: (a) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917. (b) Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161. (c) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252. (d) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712. (e) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169 and references therein, (f) Sekiguti, T.; lizuka, Y. ; Takizawa, S.; Jayaprakash, D.; Arai, T.; Sasai, H. Org. Lett. 2003, 5, 2647.
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    • note
    • Compound 4b was prepared in 76% yield from 4a by successive treatment with f-BuLi and MeI.
  • 21
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    • note
    • Molecular modeling and energy minimization were conducted using AM1 (AM1-d parameters for Ti) method within CAChe 5.04 package (Fujitsu L.T.D., 2003).
  • 23
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    • note
    • b(b′) doublet (δ 5.82) were observed for 2b and 2c, respectively. See Supporting Information.
  • 33
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    • note
    • Under similar conditions, reaction catalyzed by 2b and 2c afforded the product of 20% ee (20% conversion) and 85% ee (>98% conversion), respectively.


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