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Volumn 10, Issue 10, 2008, Pages 1935-1938

Regioselective and stereospecific synthesis of enantiopure 1,3-oxazolidin-2-ones by intramolecular ring opening of 2-(Boc-aminomethyl) aziridines. Preparation of the antibiotic linezolid

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ANTIINFECTIVE AGENT; AZIRIDINE DERIVATIVE; LINEZOLID; OXAZOLIDINONE DERIVATIVE;

EID: 47049103884     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800443p     Document Type: Article
Times cited : (34)

References (37)
  • 7
    • 33644525577 scopus 로고    scopus 로고
    • and their own references therein
    • (b) Tomasini, C.; Luppi, G.; Monari, M. J. Am. Chem. Soc. 2006, 128, 2410-2420, and their own references therein.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 2410-2420
    • Tomasini, C.1    Luppi, G.2    Monari, M.3
  • 14
    • 0037428017 scopus 로고    scopus 로고
    • Park, C. S.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Choi, D.; Lee, W. K.; Chang, J.-W.; Ha, H.-J. J. Org. Chem. 2003, 68, 43-49. In this case, (1 R,2R)-3 was used as the starting material.
    • Park, C. S.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Choi, D.; Lee, W. K.; Chang, J.-W.; Ha, H.-J. J. Org. Chem. 2003, 68, 43-49. In this case, (1 R,2R)-3 was used as the starting material.
  • 21
    • 0027517214 scopus 로고    scopus 로고
    • However, it has been reported that two N-Boc 2-substituted aziridines led to the same γ-(Boc-aminomethyl)-γ-lactone through a fully stereoselective Lewis acid catalyzed intramolecular ring-opening process quite close to that intended here on our aziridines 6: Ho, M.; Chung, J. K. K.; Tang. N. Tetrahedron Lett. 1993, 34, 6513-6516.
    • However, it has been reported that two N-Boc 2-substituted aziridines led to the same γ-(Boc-aminomethyl)-γ-lactone through a fully stereoselective Lewis acid catalyzed intramolecular ring-opening process quite close to that intended here on our aziridines 6: Ho, M.; Chung, J. K. K.; Tang. N. Tetrahedron Lett. 1993, 34, 6513-6516.
  • 22
  • 24
    • 58149193795 scopus 로고    scopus 로고
    • The absolute configurations of 2e and 2f were assigned by comparison of the sign of the specific rotation of 2e with that of an authentic sample of its enantiomer (compound 570559 in 2007-08 Aldrich catalog, in which the configuration at the N chiral center is not specified).
    • The absolute configurations of 2e and 2f were assigned by comparison of the sign of the specific rotation of 2e with that of an authentic sample of its enantiomer (compound 570559 in 2007-08 Aldrich catalog, in which the configuration at the N chiral center is not specified).
  • 25
    • 58149187075 scopus 로고    scopus 로고
    • 1H NMR spectra of the corresponding crude materials, is 75-85%.
    • 1H NMR spectra of the corresponding crude materials, is 75-85%.
  • 26
    • 58149182843 scopus 로고    scopus 로고
    • See the Supporting Information for preliminary details on this subject
    • See the Supporting Information for preliminary details on this subject.
  • 27
    • 58149191833 scopus 로고    scopus 로고
    • 2O was added.
    • 2O was added.
  • 28
    • 58149187077 scopus 로고    scopus 로고
    • Especially those proceeding from pure intermediates 7.
    • Especially those proceeding from pure intermediates 7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.