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Issue 16, 2019
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Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst

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Abstract

The mechanism of the enantioselective Michael addition of diethyl malonate to trans-β-nitrostyrene catalyzed by a tertiary amine thiourea organocatalyst is explored using experimental 13C kinetic isotope effects and density functional theory calculations. Large primary 13C KIEs on the bond-forming carbon atoms of both reactants suggest that carbon–carbon bond formation is the rate-determining step in the catalytic cycle. This work resolves conflicting mechanistic pictures that have emerged from prior experimental and computational studies.

Graphical abstract: Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst

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Publication details

The article was received on 10 Jan 2019, accepted on 07 Mar 2019 and first published on 29 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00072K
Org. Biomol. Chem., 2019,17, 3934-3939

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    Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst

    J. A. Izzo, Y. Myshchuk, J. S. Hirschi and M. J. Vetticatt, Org. Biomol. Chem., 2019, 17, 3934
    DOI: 10.1039/C9OB00072K

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