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Volumn 130, Issue 23, 2008, Pages 7449-7458

Organometallic enantiomeric scaffolding: General access to 2-substituted oxa- and azabicyclo[3.2.1]octenes via a Brønsted acid catalyzed [5 + 2] cycloaddition reaction

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; ORGANOMETALLICS;

EID: 44949244137     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800664v     Document Type: Article
Times cited : (40)

References (63)
  • 1
    • 44949088226 scopus 로고    scopus 로고
    • Organometallic enantiomeric scaffolds: (1) the metal/ligand auxiliary attached to the unsaturated ligand influences novel reactions, controls non-traditional selectivities, and provides a dominant regio- and stereocontrol element on the scaffold that allows the predictable introduction of new stereocenters at multiple sites around the unsaturated ligand, (2) a single metal/ligand auxiliary controls the introduction of multiple stereocenters over multiple steps, and (3) the organometallic nature of the scaffolding enables the use of stereodivergent tactics for the introduction of ring substituents.
    • Organometallic enantiomeric scaffolds: (1) the metal/ligand auxiliary attached to the unsaturated ligand influences novel reactions, controls non-traditional selectivities, and provides a dominant regio- and stereocontrol element on the scaffold that allows the predictable introduction of new stereocenters at multiple sites around the unsaturated ligand, (2) a single metal/ligand auxiliary controls the introduction of multiple stereocenters over multiple steps, and (3) the organometallic nature of the scaffolding enables the use of stereodivergent tactics for the introduction of ring substituents.
  • 17
    • 0004230722 scopus 로고
    • Academic Press: New York
    • Lounasmaa, M.; Tamminen, T. In Alkaloids; Academic Press: New York, 1993; pp 1-114..
    • (1993) Alkaloids , pp. 1-114
    • Lounasmaa, M.1    Tamminen, T.2
  • 23
    • 0003075009 scopus 로고    scopus 로고
    • Metz, P, Ed, Springer-Verlag: Berlin
    • Chiu, P.; Lautens, M. In Topic in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 190; pp 1-85..
    • (1997) Topic in Current Chemistry , vol.190 , pp. 1-85
    • Chiu, P.1    Lautens, M.2
  • 45
    • 44949230894 scopus 로고    scopus 로고
    • The other antipode (R)-6 would be available starting from L-arabinose following the same synthetic sequence.
    • The other antipode (R)-6 would be available starting from L-arabinose following the same synthetic sequence.
  • 50
    • 0036187765 scopus 로고    scopus 로고
    • Commercially available from Tokyo Kasei Kogyo Co., Ltd (TCI). For a reliable procedure, see: Matsuo, J.-i.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223-234.
    • Commercially available from Tokyo Kasei Kogyo Co., Ltd (TCI). For a reliable procedure, see: Matsuo, J.-i.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223-234.
  • 51
    • 44949237676 scopus 로고    scopus 로고
    • The absolute configuration of scaffolds (+)-4 and (-)-4 was determined through the synthesis of R-(-)-coniine starting from scaffold (Chemical Equation Presented)
    • The absolute configuration of scaffolds (+)-4 and (-)-4 was determined through the synthesis of R-(-)-coniine starting from scaffold (Chemical Equation Presented)
  • 52
    • 44949141192 scopus 로고    scopus 로고
    • This reagent was obtained from condensation of (S)-1-phenylbutanol with CDI in the presence of catalytic DMAP in dichloromethane. For more details, see the Supporting Information
    • This reagent was obtained from condensation of (S)-1-phenylbutanol with CDI in the presence of catalytic DMAP in dichloromethane. For more details, see the Supporting Information.
  • 53
    • 44949193494 scopus 로고    scopus 로고
    • Introduction of the chiral auxiliary directly onto compound 13 was problematic, especially at the purification stage. The sequence indicated in the text proved more flexible and allowed isolation of both racemic and chiral, nonracemic scaffolds.
    • Introduction of the chiral auxiliary directly onto compound 13 was problematic, especially at the purification stage. The sequence indicated in the text proved more flexible and allowed isolation of both racemic and chiral, nonracemic scaffolds.
  • 56
    • 44949224751 scopus 로고    scopus 로고
    • Addition of Grignard reagents at-40°C was followed by trapping of the hemiketal at - 78°C for 1 h. The reaction mixture was then allowed to warm over 2 h.
    • Addition of Grignard reagents at-40°C was followed by trapping of the hemiketal at - 78°C for 1 h. The reaction mixture was then allowed to warm over 2 h.
  • 57
    • 44949132756 scopus 로고    scopus 로고
    • 1H MR spectra.
    • 1H MR spectra.
  • 60
    • 44949196434 scopus 로고    scopus 로고
    • 2,4-Di-tert-butyl-4-hydroxytoluene (BHT), the stabilizer used in commercially available ethyl vinyl ketone, could also generate a super Brønsted acid but is assumed to be too hindered to be effective.
    • 2,4-Di-tert-butyl-4-hydroxytoluene (BHT), the stabilizer used in commercially available ethyl vinyl ketone, could also generate a "super Brønsted acid" but is assumed to be too hindered to be effective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.