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Volumn 50, Issue 32, 2011, Pages 7346-7349

Rhodium-catalyzed domino enantioselective synthesis of bicyclo[2.2.2] lactones

Author keywords

asymmetric catalysis; domino reactions; lactones; oxidation; rhodium

Indexed keywords

1 ,5-CYCLOOCTADIENE; ALLYLIC ALCOHOL; ASYMMETRIC CATALYSIS; ASYMMETRIC RING OPENING; ASYMMETRIC TRANSFORMATIONS; DOMINO REACTIONS; ENANTIOSELECTIVE SYNTHESIS; GOOD YIELD; LACTONES; RHODIUM-CATALYZED;

EID: 79960901116     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101773     Document Type: Article
Times cited : (38)

References (41)
  • 19
    • 79960900784 scopus 로고    scopus 로고
    • See the Supporting Information for full details.
    • See the Supporting Information for full details.
  • 20
    • 33748983040 scopus 로고    scopus 로고
    • The diastereomeric influence of the substituted amine nucleophile had a significant effect on the nature of the product: 5 j was a colorless oil whereas 7 j was a white solid. For an example in which this nucleophile has been used in highly diastereoselective reactions, see.
    • The diastereomeric influence of the substituted amine nucleophile had a significant effect on the nature of the product: 5 j was a colorless oil whereas 7 j was a white solid. For an example in which this nucleophile has been used in highly diastereoselective reactions, see:, S. G. Davies, G. D. Smyth, J. Chem. Soc. Perkin Trans. 1 1996, 2467-2477.
    • (1996) J. Chem. Soc. Perkin Trans. 1 , pp. 2467-2477
    • Davies, S.G.1    Smyth, G.D.2
  • 21
    • 79960899405 scopus 로고    scopus 로고
    • CCDC 816868 (5 k) and 816869 (5 n) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 816868 (5 k) and 816869 (5 n) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 22
    • 79960913492 scopus 로고    scopus 로고
    • This process is remarkable owing to the high level of steric congestion at the alkene and the regioselective isomerization of the double bond away from the amine nitrogen atom. For recent reviews on rhodium-catalyzed isomerization of allylic alcohols, see
    • This process is remarkable owing to the high level of steric congestion at the alkene and the regioselective isomerization of the double bond away from the amine nitrogen atom. For recent reviews on rhodium-catalyzed isomerization of allylic alcohols, see
  • 27
    • 79960914612 scopus 로고    scopus 로고
    • 1H NMR spectra of 11 a, indicating that the equilibrium lies towards the lactol form.
    • 1H NMR spectra of 11 a, indicating that the equilibrium lies towards the lactol form.
  • 28
    • 79960905499 scopus 로고    scopus 로고
    • There was no erosion of yield when oxygen was rigorously excluded from the reaction. See the Supporting Information for more details. For a similar example of oxidation within a rhodium-catalyzed domino sequence, see
    • There was no erosion of yield when oxygen was rigorously excluded from the reaction. See the Supporting Information for more details. For a similar example of oxidation within a rhodium-catalyzed domino sequence, see
  • 31
    • 77952362756 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 3671-3674
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 3671-3674
  • 33
    • 79960911360 scopus 로고    scopus 로고
    • For recent reviews in the subject of transition-metal catalyzed hydrogen transfer, see
    • For recent reviews in the subject of transition-metal catalyzed hydrogen transfer, see
  • 37
    • 79960913680 scopus 로고    scopus 로고
    • Selected examples
    • Selected examples


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.