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Volumn , Issue 4, 2003, Pages 570-572

A new asymmetric tridentate carbazole ligand: Its preparation and application to Nozaki-Hiyama allylation

Author keywords

Allylations; Asymmetric catalysis; Carbazole; Chromium; Nozaki Hiyama reaction; Tridentate ligand

Indexed keywords

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVITY; LIGAND BINDING; NOZAKI HIYAMA ALLYLATION; PRODUCT RECOVERY; PRODUCTIVITY; REACTION OPTIMIZATION;

EID: 0037239928     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37535     Document Type: Article
Times cited : (66)

References (28)
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    • Recent reviews: (a) Takai, K.; Nozaki, H. Proc. Jpn. Acad., Ser. B 2000, 76B, 123. (b) Fürstner, A. Chem. Rev. 1999, 99, 991. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169.
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    • Takai, K.1    Nozaki, H.2
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    • Recent reviews: (a) Takai, K.; Nozaki, H. Proc. Jpn. Acad., Ser. B 2000, 76B, 123. (b) Fürstner, A. Chem. Rev. 1999, 99, 991. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169.
    • (1999) Chem. Rev. , vol.99 , pp. 991
    • Fürstner, A.1
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    • 0032954123 scopus 로고    scopus 로고
    • Recent reviews: (a) Takai, K.; Nozaki, H. Proc. Jpn. Acad., Ser. B 2000, 76B, 123. (b) Fürstner, A. Chem. Rev. 1999, 99, 991. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169.
    • (1999) Synthesis , pp. 1
    • Wessjohann, L.A.1    Scheid, G.2
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    • 0033460956 scopus 로고    scopus 로고
    • Recent reviews: (a) Takai, K.; Nozaki, H. Proc. Jpn. Acad., Ser. B 2000, 76B, 123. (b) Fürstner, A. Chem. Rev. 1999, 99, 991. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 169
    • Avalos, M.1    Babiano, R.2    Cintas, P.3    Jimenez, J.L.4    Palacios, J.C.5
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    • note
    • 3: 458.1869, found: 458.1837.
  • 24
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    • note
    • 4, and evaporated. The residue was purified by flash chromatography (hexane/ethyl acetate = 10:1) to afford the known compound, -1-phenyl-3-buten-1-ol (64.7 mg, 71% ee, 96%): ee was determined by HPLC (254 nm); Daicel Chiral Cell OD-H 0.46 cm φ × 25 cm; hexane/iso-propanol = 19:1; flow rate=0.3 mL/min); retention time: 26.4 min for (R)-1-phenyl-3-buten-1-ol, 28.7 min for (S)-1-phenyl-3-buten-1-ol.
  • 25
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    • note
    • 3
  • 26
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    • note
    • The relationship between the reaction temperature and the solubility of the Cr(II)-ligand 1 complex and/or the related allyl complex was hard to observe under the described reaction condition because insoluble manganese powder was in the flask. Further investigation of the chromium complexes formed in situ is now under investigation.


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