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Issue 10, 2003
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Monodentate phosphoramidites; versatile ligands in catalytic asymmetric intramolecular Heck reactions

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Abstract

The Pd-catalysed intramolecular asymmetric Heck reaction (AHR) of cyclohexadienone monoacetals in the presence of chiral phosphoramidite ligands is described. High enantioselectivities (up to 96% ee) are reached with monodentate ligands. The highest selectivity is observed with Taddol-based phosphoramidites containing a small amine substituent. A study of the effect of the leaving group at the aryl moiety and a number of parameters in the AHR show that this AHR most likely proceeds through a neutral pathway and that two equiv. of ligand are necessary for optimal asymmetric induction.

Graphical abstract: Monodentate phosphoramidites; versatile ligands in catalytic asymmetric intramolecular Heck reactions

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Publication details

The article was received on 14 Jan 2003, accepted on 24 Feb 2003 and first published on 23 Apr 2003


Article type: Paper
DOI: 10.1039/B300565H
Citation: Dalton Trans., 2003,0, 2017-2023

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    Monodentate phosphoramidites; versatile ligands in catalytic asymmetric intramolecular Heck reactions

    R. Imbos, A. J. Minnaard and B. L. Feringa, Dalton Trans., 2003, 0, 2017
    DOI: 10.1039/B300565H

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