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Volumn 45, Issue 8, 2006, Pages 1248-1252

Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids

Author keywords

Amides; Chemoselectivity; Ketoacids; Ligation reactions; Peptides

Indexed keywords

CARBON DIOXIDE; CARBOXYLIC ACIDS; CONDENSATION; POLYPEPTIDES; REACTION KINETICS; SYNTHESIS (CHEMICAL); WATER;

EID: 33746190644     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503991     Document Type: Article
Times cited : (352)

References (33)
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    • b) For a solid-supported variant, see: S. Weik, J. Rademann, Angew. Chem. 2003, 115, 2595-2598;
    • (2003) Angew. Chem. , vol.115 , pp. 2595-2598
    • Weik, S.1    Rademann, J.2
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    • note
    • Although we have confirmed that epimerization of the peptide ketoacids does not occur during the reaction, the synthesis of enantiopure ketoacids presents some challenges. We have developed a new approach for their preparation that will be reported in due course.
  • 30
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    • a) For these studies, all peptide hydroxylamines were prepared from the corresponding amines by using the method of Fukuyama, which proceeds with preservation of stereochemistry, see: H. Tokuyama, T. Kuboyama, T. Fukuyama, Org. Syn. 2003, 80, 207-218;
    • (2003) Org. Syn. , vol.80 , pp. 207-218
    • Tokuyama, H.1    Kuboyama, T.2    Fukuyama, T.3
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    • O-Alkyl hydroxylamine amines can be prepared from unprotected N-bromoacetyl peptides, see: L. E. Canne, S. J. Bark, S. B. H. Kent, J. Am. Chem. Soc. 1996, 118, 5891-5896.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5891-5896
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    • note
    • Further studies on the unique reactivity and synthetic potential of the isoxazolidine substrates will be reported shortly.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.