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Volumn 131, Issue 33, 2009, Pages 11664-11665

Catalytic asymmetric synthesis of chiral tertiary organoboronic esters through conjugate boration of β-substituted cyclic enones

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSTS; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; CHIRAL BUILDING BLOCKS; DIASTEREOCONTROL; ENANTIO; ENANTIOSELECTIVE; IN-SITU; ONE POT; ORGANOBORON COMPOUND; PRODUCT YIELDS; PROTIC ADDITIVES; SEVEN-MEMBERED RINGS; THREE COMPONENT REACTIONS;

EID: 69049098113     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9045839     Document Type: Article
Times cited : (228)

References (44)
  • 3
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    • Cu-catalyzed conjugate alkylation is the main method [(a)-(k)]: (a) Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584.
    • Cu-catalyzed conjugate alkylation is the main method [(a)-(k)]: (a) Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584.
  • 20
    • 51049122384 scopus 로고    scopus 로고
    • Cu-based carbon nucleophiles generated through transmetalation exhibit high reactivity in catalytic asymmetric tetrasubstituted carbon synthesis: Shibasaki, M, Kanai, M. Chem. Rev. 2008, 108, 2853
    • Cu-based carbon nucleophiles generated through transmetalation exhibit high reactivity in catalytic asymmetric tetrasubstituted carbon synthesis: Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853.
  • 27
    • 70449362294 scopus 로고    scopus 로고
    • For other examples of the catalytic asymmetric synthesis of chiral organoboron compounds hydroboration and diboration, a
    • For other examples of the catalytic asymmetric synthesis of chiral organoboron compounds (hydroboration and diboration): (a) Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 3160
    • Lee, Y.1    Hoveyda, A.H.2
  • 36
    • 0345447210 scopus 로고    scopus 로고
    • The FDA-approved anticancer drug bortezomib is a typical example
    • The FDA-approved anticancer drug bortezomib is a typical example: Kane, R. C.; Bross, P. F.; Farrell, A. T.; Pazdur, R. The Oncologist 2003, 8, 508.
    • (2003) The Oncologist , vol.8 , pp. 508
    • Kane, R.C.1    Bross, P.F.2    Farrell, A.T.3    Pazdur, R.4
  • 39
    • 67650566923 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Hoveyda reported a relevant diastereoselective (but racemic) three-component coupling reaction involving NHC-catalyzed (Cu and protic additive-free) conjugate boration to 2-cyclohexen-1-one: Lee, K.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253.
    • During the preparation of this manuscript, Hoveyda reported a relevant diastereoselective (but racemic) three-component coupling reaction involving NHC-catalyzed (Cu and protic additive-free) conjugate boration to 2-cyclohexen-1-one: Lee, K.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253.
  • 40
    • 69049100883 scopus 로고    scopus 로고
    • For the stereochemical model, see Supporting Information SI
    • For the stereochemical model, see Supporting Information (SI).
  • 41
    • 69049091689 scopus 로고    scopus 로고
    • 6, suggesting that the Li salt does not act as an enhancer of solvent polarity.
    • 6, suggesting that the Li salt does not act as an enhancer of solvent polarity.
  • 42
    • 55549141880 scopus 로고    scopus 로고
    • Acceleration by Li salts was also observed in a Cu-catalyzed asymmetric allylcyanide addition: Yazaki, R.; Nitabaru, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 14477.
    • Acceleration by Li salts was also observed in a Cu-catalyzed asymmetric allylcyanide addition: Yazaki, R.; Nitabaru, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 14477.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.