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Volumn 12, Issue 1, 2010, Pages 172-175

Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; KETONE; LIGAND;

EID: 73949143745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9025793     Document Type: Article
Times cited : (84)

References (34)
  • 10
    • 73949115204 scopus 로고    scopus 로고
    • Initial studies on the synthesis of the diene framework by Diels-Alder cycloaddition of dienes to alkyne-based dieneophiles were discontinued because only moderate enantioselectivities were observed.
    • Initial studies on the synthesis of the diene framework by Diels-Alder cycloaddition of dienes to alkyne-based dieneophiles were discontinued because only moderate enantioselectivities were observed.
  • 17
    • 55449084881 scopus 로고    scopus 로고
    • For selected recent reports on Rh-catalyzed conjugate addition with diene-based ligands, see: (d) Okamoto, K.; Hayashi, T.; Rawal, V. H. Org. Lett. 2008, 10, 4387-41389.
    • (2008) Org. Lett. , vol.10 , pp. 4387-41389
    • Okamoto, K.1    Hayashi, T.2    Rawal, V.H.3
  • 27
    • 73949099296 scopus 로고    scopus 로고
    • Use of 1.0 equiv of KOH is optimal for reactions promoted by Rh-6.
    • Use of 1.0 equiv of KOH is optimal for reactions promoted by Rh-6.
  • 29
    • 84868072042 scopus 로고    scopus 로고
    • Diels-Alder cycloaddition promoted by 2 between β-chloroacrylate 1 and 1,3-cyclohexadiene (24 °C) results in <2% conversion.
    • Diels-Alder cycloaddition promoted by 2 between β-chloroacrylate 1 and 1,3-cyclohexadiene (24 °C) results in <2% conversion.
  • 31
    • 84868072907 scopus 로고    scopus 로고
    • 2, 24 °C).
    • 2, 24 °C).
  • 32
    • 73949143600 scopus 로고    scopus 로고
    • In select cases, Rh-12 is significantly more selective than Rh-11. For example, the reaction presented in Table 4, entry 4 promoted by Rh-11 furnishes the product with 75% ee.
    • In select cases, Rh-12 is significantly more selective than Rh-11. For example, the reaction presented in Table 4, entry 4 promoted by Rh-11 furnishes the product with 75% ee.
  • 33
    • 73949158330 scopus 로고    scopus 로고
    • For reactions promoted by Rh-12, in general, use of MeOH leads to slightly higher levels of enantioselectivity versus dioxane. For reactions presented in Table 2, MeOH was found to provide similar results as dioxane.
    • For reactions promoted by Rh-12, in general, use of MeOH leads to slightly higher levels of enantioselectivity versus dioxane. For reactions presented in Table 2, MeOH was found to provide similar results as dioxane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.