메뉴 건너뛰기




Volumn 131, Issue 19, 2009, Pages 6676-6677

Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ENANTIOSELECTIVITY; PALLADIUM; PALLADIUM COMPOUNDS;

EID: 67650550449     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9025193     Document Type: Article
Times cited : (158)

References (23)
  • 6
    • 0033591925 scopus 로고    scopus 로고
    • For a review see: (a)
    • For a review see: (a) Schultz, A. G. Chem. Commun. 1999, 1263.
    • (1999) Chem. Commun. , pp. 1263
    • Schultz, A.G.1
  • 11
    • 0035980371 scopus 로고    scopus 로고
    • A related dearomatization of an isoquinoline using an aluminium catalyst in a Reissert-type reaction has been described
    • A related dearomatization of an isoquinoline using an aluminium catalyst in a Reissert-type reaction has been described: Funabshi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10784
    • Funabshi, K.1    Ratni, H.2    Kanai, M.3    Shibasaki, M.4
  • 12
    • 0032473509 scopus 로고    scopus 로고
    • For reviews on all-carbon quaternary stereocenters, see
    • For reviews on all-carbon quaternary stereocenters, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388
    • Corey, E.J.1    Guzman-Perez, A.2
  • 16
    • 37049091222 scopus 로고
    • For a photochemical synthesis of 6-methyl-6aH-benzo[a]carbazoles and relative compounds, see
    • For a photochemical synthesis of 6-methyl-6aH-benzo[a]carbazoles and relative compounds, see: (a) Kulagowski, J. J.; Mitchell, G.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1985, 650.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 650
    • Kulagowski, J.J.1    Mitchell, G.2    Moody, C.J.3    Rees, C.W.4
  • 18
    • 84927679544 scopus 로고    scopus 로고
    • LiHMDS, NaOt-Bu, and NaHMDS also promoted this transformation, albeit with lower yields. Notably, no reaction occurred when the potassium bases were used. At present, we have no explanation for the lack of reactivity with potassium bases
    • LiHMDS, NaOt-Bu, and NaHMDS also promoted this transformation, albeit with lower yields. Notably, no reaction occurred when the potassium bases were used. At present, we have no explanation for the lack of reactivity with potassium bases.
  • 19
    • 84927685111 scopus 로고    scopus 로고
    • The use of TangPhos as a ligand led to a 26% yield of 2a, presumably because of monodentate behavior of this ligand under the reaction conditions
    • The use of TangPhos as a ligand led to a 26% yield of 2a, presumably because of monodentate behavior of this ligand under the reaction conditions.
  • 21
    • 84927678927 scopus 로고    scopus 로고
    • The ee was improved to as high as 16% in some cases. Interestingly, use of ligand L6 for compounds 1a-f led to no improvement or even a slight erosion in the ee
    • The ee was improved to as high as 16% in some cases. Interestingly, use of ligand L6 for compounds 1a-f led to no improvement or even a slight erosion in the ee.
  • 22
    • 84927680137 scopus 로고    scopus 로고
    • The crystalline sample was obtained using (S)-KenPhos
    • The crystalline sample was obtained using (S)-KenPhos.
  • 23
    • 84927681550 scopus 로고    scopus 로고
    • The absolute configuration of the major diastereomer was determined by single-crystal X-ray diffraction (see the Supporting Information)
    • The absolute configuration of the major diastereomer was determined by single-crystal X-ray diffraction (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.