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Issue 5, 2017
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Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction

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Abstract

A bis-oxazoline ligand has been complexed using Cu(II) and Zn(II) trifluoromethanesulfonate and a range of chiral ionic liquid (CIL) additives based on natural products were used as a co-catalyst for a Diels–Alder reaction. The catalytic performance of these systems was compared for the asymmetric Diels–Alder reaction between N-acryloyloxazolidinone and cyclopentadiene with and without the presence of a CIL additive. In the absence of the CIL, both catalysts resulted in low enantioselectivities in conventional solvents and ionic liquids. However, whilst only a minor effect of the CIL was observed for the Cu based catalyst, in the case of the Zn based catalyst, significant enhancements in endo enantioselectivity of up to 50% were found on the addition of a CIL.

Graphical abstract: Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction

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Publication details

The article was received on 03 Dec 2016, accepted on 21 Dec 2016 and first published on 21 Dec 2016


Article type: Paper
DOI: 10.1039/C6DT04572C
Citation: Dalton Trans., 2017,46, 1704-1713
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    Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction

    P. Goodrich, H. Q. Nimal Gunaratne, L. Hall, Y. Wang, L. Jin, M. J. Muldoon, A. P. C. Ribeiro, A. J. L. Pombeiro, V. I. Pârvulescu, P. Davey and C. Hardacre, Dalton Trans., 2017, 46, 1704
    DOI: 10.1039/C6DT04572C

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