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Volumn 15, Issue 20, 2004, Pages 3249-3256

Chiral 3-hydroxypyrrolidin-2-ones from a Baylis-Hillman adduct: Convergent, stereoselective synthesis of a glycosidase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; PHENETHYLAMINE; PYRROLIDINE DERIVATIVE; SILICA GEL;

EID: 5144235298     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.08.016     Document Type: Article
Times cited : (20)

References (63)
  • 22
    • 0032490970 scopus 로고    scopus 로고
    • A synthesis of the cis-isomer of compound 1 was also reported, which however is devoid of significant biological activity: M. Godskesen, and I. Lundt Tetrahedron Lett. 39 1998 5841 5844
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5841-5844
    • Godskesen, M.1    Lundt, I.2
  • 47
    • 5144234378 scopus 로고    scopus 로고
    • note
    • Although the coupling constants between H-3 and H-4 for trans-isomers are generally larger than for cis-isomers, the difference is small, so that a reliable configurational assignment must be performed using NOE experiments, when only one isomer is available
  • 51
    • 5144226275 scopus 로고    scopus 로고
    • note
    • This change was required owing to the lack of parameters for the Si atom
  • 52
    • 5144231728 scopus 로고    scopus 로고
    • note
    • 2) = -50.7°
  • 53
    • 5144233126 scopus 로고    scopus 로고
    • AM1 within Hyperchem 5.0-Chemplus 5.2 releases, Hypercube, Gainesville, FL, USA
    • AM1 within Hyperchem 5.0-Chemplus 5.2 releases, Hypercube, Gainesville, FL, USA
  • 54
    • 5144222965 scopus 로고    scopus 로고
    • note
    • HOMO = -8.09239 eV; F r HOMO = 8.85 × 10 - 2
  • 63
    • 5144234789 scopus 로고    scopus 로고
    • note
    • It is worth mentioning however that by raising the temperature or with longer reaction times the selection is lost and also the lactam 9 undergoes reduction


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.