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Volumn 74, Issue 9, 2009, Pages 3272-3277

Synthesis of fluoroalkene dipeptide isosteres by an intramolecular redox reaction utilizing N-Heteorocyclic carbenes (NHCs)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; DIFLUORIDE; DIPEPTIDE; DIPEPTIDE MIMETICS; FLUOROALKENES; N-HETEROCYCLIC CARBENES; PEPTIDE BONDS;

EID: 66449120549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900134k     Document Type: Article
Times cited : (35)

References (117)
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    • Although precatalysts (1a and 1b) were equally effective for the conversion, column chromatographical purification of the crude obtained by the reaction with 1b was more easily conducted than that with 1a. Therefore, we preferentially used NHC precursor 1b at the experiments described later.
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    • Although the reaction of 34b in the presence of MeOH afforded the corresponding FADI methyl ester in a slightly higher yield than that using EtOH as additive, the use of 2-propanol as an additive gave a complex mixture
    • Although the reaction of 34b in the presence of MeOH afforded the corresponding FADI methyl ester in a slightly higher yield than that using EtOH as additive, the use of 2-propanol as an additive gave a complex mixture.
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    • Attempted reaction of aldehyde 20b in the presence of 1b and DBU in EtOH at 70 °C was not completed within 2 h to give FADI 16b in 24% isolated yield.


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