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Volumn 74, Issue 9, 2009, Pages 3323-3329

Synthesis of vinylcycloheptadienes by the nickel-catalyzed three-component [3 + 2 + 2] cocyclization. Application to the synthesis of polycyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; CONJUGATED ENYNES; CYCLOHEPTANE; DIENOPHILES; HIGH YIELD; POLYCYCLIC COMPOUNDS; THREE-COMPONENT; TRIMETHYLSILYL;

EID: 66449124530     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900189g     Document Type: Article
Times cited : (38)

References (89)
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    • The configuration of the product (Eisomer) was determined by 1H NMR spectra according to previous results (see refs 17 and 18). It was also confirmed by X-ray crystallographic analyses (e.g., endo-14c and 16d).
    • The configuration of the product (Eisomer) was determined by 1H NMR spectra according to previous results (see refs 17 and 18). It was also confirmed by X-ray crystallographic analyses (e.g., endo-14c and 16d).
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    • The selective formation of a nickelacyclopentadiene intermediate and the observed regioselectivity of the product in this reaction has been previously discussed in detail. See ref 17b
    • The selective formation of a nickelacyclopentadiene intermediate and the observed regioselectivity of the product in this reaction has been previously discussed in detail. See ref 17b.
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    • The coupling product (15b) was isolated as a single isomer, but the stereochemistry has not been determined.
    • The coupling product (15b) was isolated as a single isomer, but the stereochemistry has not been determined.
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    • The selective formation of the Eisomer has been frequently observed. We assume that the s-transconformation of the EtO2C-C(R)-C(, C() bonds of 19 would be preferred. The Eisomer would be formed selectively from the s-transconformer. See ref 17b
    • The selective formation of the Eisomer has been frequently observed. We assume that the s-transconformation of the EtO2C-C(R)-C( )-C() bonds of 19 would be preferred. The Eisomer would be formed selectively from the s-transconformer. See ref 17b.


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