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Volumn 74, Issue 20, 2009, Pages 7849-7858

Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIETHYLZINC; DIORGANOZINC REAGENTS; ENAMIDES; FUNCTIONALIZATION REACTIONS; FUNCTIONALIZED; ORGANOZINC REAGENTS; REACTION COURSE; RHODIUM CATALYSTS; RHODIUM-CATALYZED;

EID: 70349881440     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901658v     Document Type: Article
Times cited : (76)

References (126)
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    • note
    • Other types of Z-enamides may be accessed efficiently through catalytic hydroamidation of terminal alkynes. See refs 11c and 11e.
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    • note
    • This hypothesis was supported by the following experiments: (i) The same reaction conducted in the presence of 5 mol % of TfOH provided tetrahydronaphthalene 68 in 88%yield. (ii) When enamide 2 was treated with 0.5 equiv of TMSOTf in the presence of 1 equiv of 2,6-lutidine, no reaction was observed.
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    • note
    • Addition of an ethyl group to the aldehyde was found to be a competing pathway with more electrophilic substrates such as benzaldehyde.


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