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Volumn 6, Issue 1, 2016, Pages 442-446

Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates

Author keywords

asymmetric catalysis; asymmetric synthesis; boron; copper; synthetic methods

Indexed keywords

BORON; CATALYSIS; ENANTIOSELECTIVITY; PHOSPHORUS COMPOUNDS;

EID: 84953341812     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b02742     Document Type: Article
Times cited : (159)

References (59)
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    • For the only previous example of enantioselective 1,6-copper-catalyzed borylation of acyclic α,β,δ,γ-unsaturated esters, see: Luo, Y.; Roy, I. D.; Madec, A. G. E.; Lam, H. W. Angew. Chem., Int. Ed. Engl. 2014, 53, 4186 10.1002/anie.201310380
    • (2014) Angew. Chem., Int. Ed. Engl. , vol.53 , pp. 4186
    • Luo, Y.1    Roy, I.D.2    Madec, A.G.E.3    Lam, H.W.4
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    • For a recent highlight, see: Parra, A.; Tortosa, M. ChemCatChem 2015, 7, 1524 10.1002/cctc.201500176
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    • Asymmetric Synthesis of Versatil Benzylic Boronic Esters through a Borylation-Aromation Process
    • Presented at the, Lisboa, Spain, July 12-16, Paper No. P181
    • López, A.; Jarava, C.; Parra, A.; Cruz, F.; Tortosa, M. Asymmetric Synthesis of Versatil Benzylic Boronic Esters through a Borylation-Aromation Process. Presented at the 19th European Symposium of Organic Chemistry (ESOC2015), Lisboa, Spain, July 12-16, 2015; Paper No. P181.
    • (2015) 19th European Symposium of Organic Chemistry (ESOC2015)
    • López, A.1    Jarava, C.2    Parra, A.3    Cruz, F.4    Tortosa, M.5
  • 56
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    • Asymmetric Synthesis of Versatil Benzylic Boronic Esters through a Borylation-Aromatization Process
    • Presented at the, A Coruña, Spain, July 19-23, Paper No. S3-FC-12
    • Jarava, C.; López, A.; Parra, A.; Cruz, F.; Tortosa, M. Asymmetric Synthesis of Versatil Benzylic Boronic Esters through a Borylation-Aromatization Process. Presented at the XXXV Spanish Biannual Chemistry Congress, A Coruña, Spain, July 19-23, 2015; Paper No. S3-FC-12.
    • (2015) XXXV Spanish Biannual Chemistry Congress
    • Jarava, C.1    López, A.2    Parra, A.3    Cruz, F.4    Tortosa, M.5
  • 57
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    • During the preparation of this manuscript, Liao et al. published a closely related paper using a sulfoxide-phosphine ligand (published online Aug. 28, 2015): Lou, Y.; Cao, P.; Jia, T.; Zhang, Y.; Wang, M.; Liao, J. Angew. Chem., Int. Ed. 2015, 54, 12134. 10.1002/anie.201505926 We have observed similar enantioselectivities using a commercially available ligand and running the reaction at room temperature. In addition, our catalytic system can overcome some of the structural limitations found in the excellent work by Liao.
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 12134
    • Lou, Y.1    Cao, P.2    Jia, T.3    Zhang, Y.4    Wang, M.5    Liao, J.6
  • 58
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    • For a review on the use of the t-Bu group as a protecting group in the synthesis of aromatic compounds, see: Saleh, S. A.; Tashtoush, H. I. Tetrahedron 1998, 54, 14157 10.1016/S0040-4020(98)00756-X
    • (1998) Tetrahedron , vol.54 , pp. 14157
    • Saleh, S.A.1    Tashtoush, H.I.2
  • 59
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    • CCDC 1405406 contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html. The absolute configuration of the other dibenzylic boronates was assigned by analogy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.