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Volumn 44, Issue 8, 2003, Pages 1545-1548

Preparation and properties of chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains

Author keywords

Chemoselectivity; Combinatorial chemistry; Desymmetrization; Nucleophilic catalyst; Pyrrolidinopyridine

Indexed keywords

1,3 CYCLOHEXANODIOL; 4 PYRROLIDINOPYRIDINE DERIVATIVE; CYCLOHEXANOL DERIVATIVE; FUNCTIONAL GROUP; HYDROXYPROLINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037450486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00021-2     Document Type: Article
Times cited : (84)

References (35)
  • 1
    • 0002378156 scopus 로고
    • For a leading reference of asymmetric acylation of alcohols:
    • For a leading reference of asymmetric acylation of alcohols: Ichikawa J., Asami M., Mukaiyama T. Chem. Lett. 1984;949.
    • (1984) Chem. Lett. , pp. 949
    • Ichikawa, J.1    Asami, M.2    Mukaiyama, T.3
  • 19
    • 0013036507 scopus 로고    scopus 로고
    • For examples, acylative kinetic resolution of racemic-3 catalyzed by 20 and 21 proceeds with selectivity factors of 11 and 1.6, respectively, see Ref. 4.
    • For examples, acylative kinetic resolution of racemic-3 catalyzed by 20 and 21 proceeds with selectivity factors of 11 and 1.6, respectively, see Ref. 4.
  • 22
    • 0013031496 scopus 로고    scopus 로고
    • While 1,5-disubsituted imidazoles are known to be active nucleophilic catalysts (Ref. 7), 1,4-disubsituted surrogates are not.
    • While 1,5-disubsituted imidazoles are known to be active nucleophilic catalysts (Ref. 7), 1,4-disubsituted surrogates are not.
  • 25
    • 0012942196 scopus 로고    scopus 로고
    • For examples, acylative kinetic resolution of racemic-3 with isobutyric anhydride was promoted by 5 mol% of 8, 9, and 10 to give (1S, 2R)-3 in 88% ee at 68% conversion (s=6.3), in 83% ee at 67% conversion (s=5.6), and in 99% ee at 78% conversion (s=7.6), respectively.
    • For examples, acylative kinetic resolution of racemic-3 with isobutyric anhydride was promoted by 5 mol% of 8, 9, and 10 to give (1S, 2R)-3 in 88% ee at 68% conversion (s=6.3), in 83% ee at 67% conversion (s=5.6), and in 99% ee at 78% conversion (s=7.6), respectively.
  • 26
    • 0013031580 scopus 로고    scopus 로고
    • note
    • +), found m/z 619.2875.
  • 28
    • 0002658793 scopus 로고
    • For examples of nonenzymatic acylative desymmetrization of meso-diols, see: (a) Terashima, S.; Yamada, S. Tetrahedron Lett. 1977, 18, 1001;
    • (1977) Tetrahedron Lett. , vol.18 , pp. 1001
    • Terashima, S.1    Yamada, S.2
  • 33
    • 0012942197 scopus 로고    scopus 로고
    • R=65, 67 min.
    • R=65, 67 min.
  • 34
    • 0012935174 scopus 로고    scopus 로고
    • Similar cooperative effect, albeit less significant, was observed in the acylation of 14 with 10 in toluene: Kinetic resolution of racemic-15 with 10 in toluene gave recovered 15 in 18% ee at 47% conversion (s=1.8) whose absolute configuration was same as that obtained by mono-acylation of 14 with 10.
    • Similar cooperative effect, albeit less significant, was observed in the acylation of 14 with 10 in toluene: Kinetic resolution of racemic-15 with 10 in toluene gave recovered 15 in 18% ee at 47% conversion (s=1.8) whose absolute configuration was same as that obtained by mono-acylation of 14 with 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.