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Issue 39, 2011
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The origin of regio- and enantioselectivity in the Rh/chiral 1,4-diene-catalyzed addition of phenylboronic acid to enones: insights from DFT

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Abstract

A density functional theory study of the addition of phenylboronic acid to cyclohexenone catalyzed by chiral 1,4-diene–Rh(I) catalyst reveals that 1,4-addition is thermodynamically preferred. The enthalpy-driven enantioselection occurs during the carborhodation step and not the enone binding step, as previously proposed. The chiral ligand selectively destabilizes the disfavored transition state by making it “more early”.

Graphical abstract: The origin of regio- and enantioselectivity in the Rh/chiral 1,4-diene-catalyzed addition of phenylboronic acid to enones: insights from DFT

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Publication details

The article was received on 21 Jun 2011, accepted on 11 Aug 2011 and first published on 08 Sep 2011


Article type: Communication
DOI: 10.1039/C1CC13702F
Chem. Commun., 2011,47, 10969-10971

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    The origin of regio- and enantioselectivity in the Rh/chiral 1,4-diene-catalyzed addition of phenylboronic acid to enones: insights from DFT

    E. A. B. Kantchev, Chem. Commun., 2011, 47, 10969
    DOI: 10.1039/C1CC13702F

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