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Volumn 9, Issue 3, 2011, Pages 739-743

Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; AZETIDINONES; CHIRAL AUXILIARIES; DEPROTECTION; ENAMINES; LOW COSTS; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; STRUCTURAL FEATURE; TRICHLOROSILANES;

EID: 79251481185     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00570c     Document Type: Article
Times cited : (43)

References (58)
  • 6
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    • Ed., all issue
    • For a special issue on hydrogenation and transfer hydrogenation see: M. J. Krische Y. Sun Acc. Chem. Res. 2007 40 12 1237
    • (2007) Acc. Chem. Res. , vol.40 , Issue.12 , pp. 1237
    • Krische, M.J.1    Sun, Y.2
  • 10
    • 77950252084 scopus 로고    scopus 로고
    • Recent examples of organometallic catalysis in carbon-nitrogen double bond: A. Baeza A. Pfaltz Chem.-Eur. J. 2010 16 4003
    • (2010) Chem.-Eur. J. , vol.16 , pp. 4003
    • Baeza, A.1    Pfaltz, A.2
  • 48
    • 79251495272 scopus 로고    scopus 로고
    • European Patent Application November 30 2007; PCT/EP/2008/010079, Nov. 27, 2008. WO2009068284 (A2), 2009-06-04
    • S. Guizzetti, M. Benaglia, European Patent Application November 30 2007; PCT/EP/2008/010079, Nov. 27, 2008. WO2009068284 (A2), 2009-06-04
    • Guizzetti, S.1    Benaglia, M.2
  • 49
    • 79251513118 scopus 로고    scopus 로고
    • European Patent Appl. n.EP07023240.0, September 22, 2008
    • S. Guizzetti, M. Benaglia, European Patent Appl. n.EP07023240.0, September 22, 2008
    • Guizzetti, S.1    Benaglia, M.2
  • 50
    • 79251532252 scopus 로고    scopus 로고
    • For the preparation of enamines see details in ESI
    • For the preparation of enamines see details in ESI
  • 51
    • 79251519131 scopus 로고    scopus 로고
    • The reduction of N-phenyl enamine in the same experimental conditions led to the corresponding β-amino ester in better yields (88%) and moderately higher enantioselectivities (80% e.e.)
    • he reduction of N-phenyl enamine in the same experimental conditions led to the corresponding β-amino ester in better yields (88%) and moderately higher enantioselectivities (80% e.e.).
  • 55
    • 79251491538 scopus 로고    scopus 로고
    • The favourably match or mismatch combinations of chiral amine auxiliary and catalysts have been already clarified in ref. 9d. The reduction of chiral enamine 5 with achiral Lewis base, such as DMF, at 0 °C in our hands afforded the reduction product in 53% diastereoisomeric ratio
    • The favourably match or mismatch combinations of chiral amine auxiliary and catalysts have been already clarified in ref. 9d. The reduction of chiral enamine 5 with achiral Lewis base, such as DMF, at 0 °C in our hands afforded the reduction product in 53% diastereoisomeric ratio.
  • 57
    • 79251480914 scopus 로고    scopus 로고
    • The quality and the age of Pd/C are critical elements influencing the reaction efficiency; the experimental conditions are very dependent on the activity of the catalyst (5-15 atm, Pd/C, EtOH, 4-12 h, RT)
    • The quality and the age of Pd/C are critical elements influencing the reaction efficiency; the experimental conditions are very dependent on the activity of the catalyst (5-15 atm, Pd/C, EtOH, 4-12 h, RT).
  • 58
    • 79251500842 scopus 로고    scopus 로고
    • See also ref. 9e See ESI for HPLC traces and spectroscopic details
    • See also ref. 9e See ESI for HPLC traces and spectroscopic details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.