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Volumn 19, Issue 9, 2013, Pages 3204-3214

Exceptionally E- and β-selective NHC-Cu-catalyzed proto-silyl additions to terminal alkynes and site- and enantioselective proto-boryl additions to the resulting vinylsilanes: Synthesis of enantiomerically enriched vicinal and geminal borosilanes

Author keywords

boron; borosilanes; copper; enantioselective catalysis; silicon; synthesis

Indexed keywords

ANTI-BACTERIAL AGENTS; ARYL SUBSTITUENTS; BOROSILANES; CATALYTIC METHODS; CATALYTIC PROCESS; COPPER COMPLEXES; CU COMPLEXES; CU-BASED CATALYST; DIFFERENT CLASS; ENANTIOMERIC RATIO; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; HIGH ENANTIOSELECTIVITY; IMIDAZOLINIUM SALTS; MONODENTATES; N-HETEROCYCLIC CARBENES; NATURALLY OCCURRING; PROTOSILYLATION; TERMINAL ALKYNE; VINYL SILANE; WORKING MODELS;

EID: 84874057367     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203803     Document Type: Article
Times cited : (128)

References (86)
  • 3
    • 79960623973 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 7079-7082.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7079-7082
  • 4
    • 73249139284 scopus 로고    scopus 로고
    • Y. Lee, H. Jang, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 18234-18235; for an application of NHC-Cu-catalyzed enantioselective protoboration of a vinylboron species in the preparation of a biologically active molecule, see
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18234-18235
    • Lee, Y.1    Jang, H.2    Hoveyda, A.H.3
  • 8
    • 33744502921 scopus 로고    scopus 로고
    • For initial disclosures regarding site-selective addition of an NHC-Cu-B(pin)to an alkene (styrene), see:, D. S. Laitar, E. Y. Tsui, J. P. Sadighi, Organometallics 2006, 25, 2405-2408.
    • (2006) Organometallics , vol.25 , pp. 2405-2408
    • Laitar, D.S.1    Tsui, E.Y.2    Sadighi, J.P.3
  • 14
    • 84862067111 scopus 로고    scopus 로고
    • For other catalytic (non-enantioselective) methods for synthesis of borosilanes, see:, H.-Y. Jung, J. Yun, Org. Lett. 2012, 14, 2606-2609.
    • (2012) Org. Lett. , vol.14 , pp. 2606-2609
    • Jung, H.-Y.1    Yun, J.2
  • 18
    • 54749136535 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7424-7427
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7424-7427
  • 19
    • 84859855352 scopus 로고    scopus 로고
    • J. K. Park, D. T. McQuade, Synthesis 2012, 44, 1485-1490; for an efficient (non-catalytic) method for enantioselective synthesis of geminal borosilanes, see
    • (2012) Synthesis , vol.44 , pp. 1485-1490
    • Park, J.K.1    McQuade, D.T.2
  • 21
    • 79957681266 scopus 로고    scopus 로고
    • For an example of a strong influence exerted by a catalyst's structure on the outcome of NHC-Cu-catalyzed protoborations of terminal alkynes, see:, H. Jang, A. R. Zhugralin, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 7859-7871.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7859-7871
    • Jang, H.1    Zhugralin, A.R.2    Lee, Y.3    Hoveyda, A.H.4
  • 25
    • 0000024647 scopus 로고
    • Enantioselective hydroboration reactions of vinyl(trimethyl)silanes in the presence of stoichiometric amounts of a chiral borohydride reagent have been reported (up to >98 % geminal selectivity and 70:30 e.r.). See:, J. A. Soderquist, S.-J. H. Lee, Tetrahedron 1988, 44, 4033-4042.
    • (1988) Tetrahedron , vol.44 , pp. 4033-4042
    • Soderquist, J.A.1    Lee, S.-J.H.2
  • 29
    • 77951169903 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2978-2986.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2978-2986
  • 31
  • 32
    • 17744395347 scopus 로고    scopus 로고
    • B. M. Trost, Z. T. Ball, Synthesis 2005, 853-887; for an α-selective catalytic hydrosilylation of terminal alkynes, see
    • (2005) Synthesis , pp. 853-887
    • Trost, B.M.1    Ball, Z.T.2
  • 43
    • 77955564531 scopus 로고    scopus 로고
    • For examples of site selective aluminum-hydride additions to terminal alkynes, see:, F. Gao, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 10961-10963 and references cited therein.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 10961-10963
    • Gao, F.1    Hoveyda, A.H.2
  • 44
    • 33750292358 scopus 로고    scopus 로고
    • For the initial observation that in situ reaction of a copper-alkyl complex with MeOH can lead to re-generation of the corresponding Cu-OMe, which leads to re-formation of the requisite Cu-B(pin), see:, S. Mun, J.-E. Lee, J. Yun, Org. Lett. 2006, 8, 4887-4889.
    • (2006) Org. Lett. , vol.8 , pp. 4887-4889
    • Mun, S.1    Lee, J.-E.2    Yun, J.3
  • 45
    • 84856303686 scopus 로고    scopus 로고
    • 2, re-generation of NHC-Cu-B(pin) can occur through reaction of the NHC-Cu-alkoxide with the sodium boronate derived from addition of NaOtBu or NaOMe with the diboron reagent. See:, B. Jung, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 1490-1493 for related discussions.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 1490-1493
    • Jung, B.1    Hoveyda, A.H.2
  • 55
    • 79953854839 scopus 로고    scopus 로고
    • J. A. Dabrowski, F. Gao, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 4778-4781. For enantioselective synthesis of allylsilanes through Cu-catalyzed conjugate addition reactions, see
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 4778-4781
    • Dabrowski, J.A.1    Gao, F.2    Hoveyda, A.H.3
  • 63
    • 79952543808 scopus 로고    scopus 로고
    • For utilization of mixed organoaluminum reagents in enantioselective Cu-catalyzed reactions, see:, F. Gao, Y. Lee, K. Mandai, A. H. Hoveyda, Angew. Chem. 2010, 122, 8548-8552
    • (2010) Angew. Chem. , vol.122 , pp. 8548-8552
    • Gao, F.1    Lee, Y.2    Mandai, K.3    Hoveyda, A.H.4
  • 64
    • 78149439210 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 8370-8374.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8370-8374
  • 73
    • 0030007621 scopus 로고    scopus 로고
    • For a review on oxidation of C-Si bonds, see:, G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599-7662.
    • (1996) Tetrahedron , vol.52 , pp. 7599-7662
    • Jones, G.R.1    Landais, Y.2
  • 76
    • 0000889931 scopus 로고
    • W. P. Griffith, Chem. Soc. Rev. 1992, 21, 179-185. For a review on oxidation reactions catalyzed by tetrapropylammonium perruthenate, see
    • (1992) Chem. Soc. Rev. , vol.21 , pp. 179-185
    • Griffith, W.P.1
  • 82
    • 84874023284 scopus 로고    scopus 로고
    • Ref. [30a]
    • Ref. [30a]
  • 84
    • 84874068432 scopus 로고    scopus 로고
    • N. W. Mszar, A. H. Hoveyda, unpublished results
    • N. W. Mszar, A. H. Hoveyda, unpublished results.


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