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Issue 52, 2014
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Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence

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Abstract

A highly stereoselective one-pot procedure involving an enantioselective Michael addition promoted by low loading of an amino-squaramide catalyst followed by an achiral base catalyzed domino Michael–Knoevenagel-type 1,2-addition sequence provides efficient access to fully substituted cyclohexanes bearing five contiguous stereogenic centers in good yields (68–86%) and excellent stereoselectivities (>30 : 1 dr and 96–99% ee).

Graphical abstract: Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence

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Publication details

The article was received on 13 Mar 2014, accepted on 14 May 2014 and first published on 15 May 2014


Article type: Communication
DOI: 10.1039/C4CC01885K
Citation: Chem. Commun., 2014,50, 6853-6855
  • Open access: Creative Commons BY license
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    Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael–Michael–1,2-addition sequence

    P. Chauhan, G. Urbanietz, G. Raabe and D. Enders, Chem. Commun., 2014, 50, 6853
    DOI: 10.1039/C4CC01885K

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