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Volumn 132, Issue 34, 2010, Pages 11926-11928

Stereoselective syntheses of trisubstituted olefins via platinum catalysis: α-Silylenones with geometrical complementarity

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; REGIO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; SYNTHETIC UTILITY;

EID: 77956088267     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1058197     Document Type: Article
Times cited : (76)

References (52)
  • 1
    • 77956075809 scopus 로고    scopus 로고
    • For select reviews on Pt and Au catalysis in alkyne activation, see
    • For select reviews on Pt and Au catalysis in alkyne activation, see
  • 6
    • 51249100498 scopus 로고    scopus 로고
    • Arcadi, A. Chem. Rev. 2008, 108, 3266-3325
    • (2008) Chem. Rev. , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 10
  • 12
    • 77956069695 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 13
    • 77956083863 scopus 로고    scopus 로고
    • 2. Olefin isomerization occurred to some extent when the enone products were resubjected to the reaction conditions
    • 2. Olefin isomerization occurred to some extent when the enone products were resubjected to the reaction conditions.
  • 15
    • 77956092391 scopus 로고    scopus 로고
    • 2O-catalyzed silicon migration, but in modest yield and low stereoselectivity. See
    • 2O-catalyzed silicon migration, but in modest yield and low stereoselectivity. See
  • 20
    • 77956074313 scopus 로고    scopus 로고
    • In general, isomerization to thermodynamic equilibrium led to an approximately 2:1 mixture of E and Z enone isomers
    • In general, isomerization to thermodynamic equilibrium led to an approximately 2:1 mixture of E and Z enone isomers.
  • 22
    • 77956092983 scopus 로고    scopus 로고
    • For a recent discussion, see
    • For a recent discussion, see
  • 25
    • 77956076587 scopus 로고    scopus 로고
    • Most hydrosilylation studies of internal alkynes have achieved regioselectivities primarily through either steric discrimination or intramolecular delivery of tethered silanes. For catalytic regioselective hydrosilylations of internal alkynes apparently reliant on electronic differentiation, see
    • Most hydrosilylation studies of internal alkynes have achieved regioselectivities primarily through either steric discrimination or intramolecular delivery of tethered silanes. For catalytic regioselective hydrosilylations of internal alkynes apparently reliant on electronic differentiation, see
  • 29
    • 77956077501 scopus 로고    scopus 로고
    • Tius has described a rhodium-catalyzed hydrosilylation of ynals to provide similar α-selectivity to our system, but steric differentiation was also highly influential. See
    • Tius has described a rhodium-catalyzed hydrosilylation of ynals to provide similar α-selectivity to our system, but steric differentiation was also highly influential. See
  • 31
    • 77956090446 scopus 로고    scopus 로고
    • Although geometrical considerations are not applicable, it should be noted that substrates based on terminal alkynes were effective in the silyl migration process but provided complex mixtures in the hydrosilylation process. See Supporting Information for details
    • Although geometrical considerations are not applicable, it should be noted that substrates based on terminal alkynes were effective in the silyl migration process but provided complex mixtures in the hydrosilylation process. See Supporting Information for details.
  • 32
    • 77956074140 scopus 로고    scopus 로고
    • For a review of the use of α-substituted enones in cross-coupling reactions, see
    • For a review of the use of α-substituted enones in cross-coupling reactions, see
  • 34
    • 77956078446 scopus 로고    scopus 로고
    • For select reviews, see
    • For select reviews, see
  • 45
    • 77956069093 scopus 로고    scopus 로고
    • The silylenone products were not effective Hiyama coupling partners, likely due to the complicating electrophilicity of the enone under the fluoride-based conditions
    • The silylenone products were not effective Hiyama coupling partners, likely due to the complicating electrophilicity of the enone under the fluoride-based conditions.
  • 46
    • 77956093849 scopus 로고    scopus 로고
    • Water additive was crucial to the success of these transformations, most likely facilitating the formation of a disiloxane intermediate which upon fluoride activation is the active transmetallation species. For a relevant discussion, see
    • Water additive was crucial to the success of these transformations, most likely facilitating the formation of a disiloxane intermediate which upon fluoride activation is the active transmetallation species. For a relevant discussion, see
  • 48
    • 77956081715 scopus 로고    scopus 로고
    • Silylenones can also be converted to α-iodoenones by treatment with ICl; see
    • α-Silylenones can also be converted to α-iodoenones by treatment with ICl; see
  • 50
    • 77956082026 scopus 로고    scopus 로고
    • This process is generally stereoconvergent, however, as illustrated in the transformations of both 3 and 10 to 11. In contrast, the use of Hiyama couplings enables efficient access to both isomers of the trisubstituted alkenes
    • This process is generally stereoconvergent, however, as illustrated in the transformations of both 3 and 10 to 11. In contrast, the use of Hiyama couplings enables efficient access to both isomers of the trisubstituted alkenes.
  • 51
    • 77956079805 scopus 로고    scopus 로고
    • For a related example of accessing alkenes with geometrical complementarity via alkyne activation processes, see
    • For a related example of accessing alkenes with geometrical complementarity via alkyne activation processes, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.