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Volumn 132, Issue 38, 2010, Pages 13152-13153

Copper-catalyzed regio-and enantioselective synthesis of chiral enol acetates and β-substituted aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALKYLATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; GRIGNARD REAGENT; IN-SITU; ONE-POT PROTOCOL; UNSATURATED ALDEHYDES;

EID: 77957138785     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja105585y     Document Type: Article
Times cited : (41)

References (18)
  • 8
    • 29144442530 scopus 로고    scopus 로고
    • For an example of a catalytic enantioselective 1,4-addition of organozinc compouds to enals, see:, For Rh-catalyzed asymmetric 1,4-additions, see:, J. Am. Chem. Soc. 2005, 127, 10850
    • For an example of a catalytic enantioselective 1,4-addition of organozinc compouds to enals, see: Bräse, S. and Höfener, S. Angew. Chem., Int. Ed. 2005, 44, 7879 For Rh-catalyzed asymmetric 1,4-additions, see: Paquin, J.-F., Defieber, C., Stephenson, C. R. J., and Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7879
    • Bräse, S.1    Höfener, S.2    Paquin, J.-F.3    Defieber, C.4    Stephenson, C.R.J.5    Carreira, E.M.6
  • 10
    • 77951835421 scopus 로고    scopus 로고
    • Recently, a Cu-catalyzed asymmetric conjugate addition of Grignard reagents to enals with modest selectivities and yields was described. See
    • Recently, a Cu-catalyzed asymmetric conjugate addition of Grignard reagents to enals with modest selectivities and yields was described. See: Palais, L., Babel, L., Quintard, A., Belot, S., and Alexakis, A. Org. Lett. 2010, 12, 1988
    • (2010) Org. Lett. , vol.12 , pp. 1988
    • Palais, L.1    Babel, L.2    Quintard, A.3    Belot, S.4    Alexakis, A.5
  • 11
    • 77957128346 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 12
    • 77950202999 scopus 로고    scopus 로고
    • For a recent review of phosphoramidites, see
    • For a recent review of phosphoramidites, see: Teichert, J. F. and Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 2486
    • Teichert, J.F.1    Feringa, B.L.2
  • 13
    • 77957129859 scopus 로고    scopus 로고
    • As the substrate is a racemic chloroacetate, it is probable that in situ racemization of the starting material or isomerization of the copper intermediate occurs during slow addition of the Grignard reagent. Because of the high sensitivity of the in situ-formed chloroacetate, to date it has not been possible to monitor the ee of the substrate during the reaction (kinetic resolution)
    • As the substrate is a racemic chloroacetate, it is probable that in situ racemization of the starting material or isomerization of the copper intermediate occurs during slow addition of the Grignard reagent. Because of the high sensitivity of the in situ-formed chloroacetate, to date it has not been possible to monitor the ee of the substrate during the reaction (kinetic resolution).
  • 16
    • 77957126260 scopus 로고    scopus 로고
    • It has been shown that the regioselectivity of the copper-catalyzed addition of MeMgBr to cinnamyl-type allylic chlorides is lower than for other alkyl Grignard reagents. See
    • It has been shown that the regioselectivity of the copper-catalyzed addition of MeMgBr to cinnamyl-type allylic chlorides is lower than for other alkyl Grignard reagents. See: Tissot-Crosset, K. and Alexakis, A. Tetrahedron Lett. 2004, 45, 7377
    • (2004) Tetrahedron Lett. , vol.45 , pp. 7377
    • Tissot-Crosset, K.1    Alexakis, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.