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Issue 26, 2012
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The effects of solvent on switchable stereoselectivity: copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands

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Abstract

A highly enantioselective copper-catalyzed conjugate addition of diethylzinc to acyclic aromatic enones was developed with phosphoramidite ligands bearing a D2-symmetric biphenyl backbone. This type of reaction demonstrated that toluene and THF solvents can completely reverse the absolute configuration of the products, thus simplifying the process of accessing either enantiomer (S: 92% ee, 94% yield; R: 99% ee, 96% yield).

Graphical abstract: The effects of solvent on switchable stereoselectivity: copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands

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Publication details

The article was received on 14 Apr 2012, accepted on 06 May 2012 and first published on 08 May 2012


Article type: Paper
DOI: 10.1039/C2OB25730K
Citation: Org. Biomol. Chem., 2012,10, 5137-5142
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    The effects of solvent on switchable stereoselectivity: copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands

    H. Yu, F. Xie, Z. Ma, Y. Liu and W. Zhang, Org. Biomol. Chem., 2012, 10, 5137
    DOI: 10.1039/C2OB25730K

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