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Volumn 60, Issue 20, 2004, Pages 4513-4525

New atropisomeric biaryl derivatives of 4-aminopyridine - Identification of an improved nucleophilic catalyst for asymmetric acylation of sec-alcohols

Author keywords

Acylation; Asymmetric catalysis; Atropisomerism; Esterification; Nucleophilic catalysis; sec Alcohols

Indexed keywords

1 (1 NAPHTHYL)ETHANOL; 1 (2 TOLYL)ETHANOL; 1 (2,6 DIMETHYLPHENYL)ETHANOL; 2,2 DIMETHYL 1 PHENYLPROPAN 1 OL; 3 CHLORO 1 PHENYLPROPAN 1 OL; 4 AMINOPYRIDINE DERIVATIVE; ALCOHOL DERIVATIVE; BUTYLAMINE; FLUOXETINE; INDAN 1 OL; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

EID: 1942468801     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.098     Document Type: Article
Times cited : (83)

References (57)
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  • 41
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    • note
    • Our original hypothesis for the differing levels of selectivity displayed by these two catalyst series was that the 5-azaindoline-based catalysts ( VIII, Figure 1) provided less effective left-from-right differentiation than the corresponding 4-diethylaminopyridine-based catalysts ( IX, Figure 1). See Ref. 30. We still envisage that this is an important factor.
  • 42
    • 1942509466 scopus 로고    scopus 로고
    • note
    • Interestingly, in the crystal structure of the salt of (-)-6c with N-Boc-O-benzyl-(S)-tyrosine the diethylamino substituent occupies an alternative chiral conformation in which both ethyl groups are angled away from the phenyl substituent (see Ref. 29).
  • 44
    • 1942541282 scopus 로고    scopus 로고
    • note
    • The identity of pyridine 9c was unambiguously secured by a single crystal X-ray structure determination. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 220843. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax:+44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
  • 45
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    • Muller, T.E.1    Beller, M.2
  • 47
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    • The fused benzenoid ring takes priority over the 2-phenyl substituent when assigning the naphthyl end of the biaryl axis by Cahn-Ingold-Prelog (CIP) priority rules, see: New York: Wiley. p. 107
    • The fused benzenoid ring takes priority over the 2-phenyl substituent when assigning the naphthyl end of the biaryl axis by Cahn-Ingold-Prelog (CIP) priority rules, see: Eliel E.L., Wilen S.H. Stereochemistry of organic compounds. 1994;Wiley, New York. p. 107.
    • (1994) Stereochemistry of Organic Compounds
    • Eliel, E.L.1    Wilen, S.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.