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Volumn 16, Issue 11, 2014, Pages 3146-3149

Silyl imine electrophiles in enantioselective catalysis: A rosetta stone for peptide homologation, enabling diverse N-protected aryl glycines from aldehydes in three steps

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; BROMONITROMETHANE; DRUG DERIVATIVE; ETHANE; GLYCINE; NITRO DERIVATIVE; PEPTIDE; SILICON DERIVATIVE;

EID: 84902105417     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501297a     Document Type: Article
Times cited : (26)

References (51)
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    • For a review of emerging methods in amide and peptide synthesis, see
    • For a review of emerging methods in amide and peptide synthesis, see: Bode, J. W. Curr. Opin. Drug Discovery Dev. 2006, 9, 765
    • (2006) Curr. Opin. Drug Discovery Dev. , vol.9 , pp. 765
    • Bode, J.W.1
  • 16
    • 0002858266 scopus 로고    scopus 로고
    • Recent developments in the enantioselective synthesis of non-natural amino acids: Sharpless aminohydroxylation
    • Recent developments in the enantioselective synthesis of non-natural amino acids: Sharpless aminohydroxylation: Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1207
    • Reddy, K.L.1    Sharpless, K.B.2
  • 39
    • 0033559915 scopus 로고    scopus 로고
    • However, Brown's subsequent work revealed the importance of water in this reaction, suggesting that addition occurs after hydrolytic cleavage of the silyl protecting group. Therefore, enantioselective addition occurs to the free aldimine/borane complex, not to the putitive N -TMS imine
    • However, Brown's subsequent work revealed the importance of water in this reaction, suggesting that addition occurs after hydrolytic cleavage of the silyl protecting group. Therefore, enantioselective addition occurs to the free aldimine/borane complex, not to the putitive N -TMS imine: Chen, G. M.; Ramachandran, P. V.; Brown, H. C. Angew. Chem., Int. Ed. 1999, 38, 825
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 825
    • Chen, G.M.1    Ramachandran, P.V.2    Brown, H.C.3
  • 47
    • 78650406485 scopus 로고    scopus 로고
    • For similar observations with an indolenine electrophile, see
    • For similar observations with an indolenine electrophile, see: Dobish, M. C.; Johnston, J. N. Org. Lett. 2010, 12, 5744
    • (2010) Org. Lett. , vol.12 , pp. 5744
    • Dobish, M.C.1    Johnston, J.N.2
  • 51
    • 77953146184 scopus 로고    scopus 로고
    • To the best of our knowledge, only one enantioselective synthesis of α-amino acids has shown some degree of tolerance to Fmoc protection directly (two substrates, hydrogenation to phenylalanine derivatives)
    • To the best of our knowledge, only one enantioselective synthesis of α-amino acids has shown some degree of tolerance to Fmoc protection directly (two substrates, hydrogenation to phenylalanine derivatives): Fernández-Pérez, H.; Donald, S. M. A.; Munslow, I. J.; Benet-Buchholz, J.; Maseras, F.; Vidal-Ferran, A. Chem.-Eur. J. 2010, 16, 6495
    • (2010) Chem.-Eur. J. , vol.16 , pp. 6495
    • Fernández-Pérez, H.1    Donald, S.M.A.2    Munslow, I.J.3    Benet-Buchholz, J.4    Maseras, F.5    Vidal-Ferran, A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.