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  • Title: Using chiral ionic liquid additives to enhance asymmetric induction in a Diels-Alder reaction.
    Author: Goodrich P, Nimal Gunaratne HQ, Hall L, Wang Y, Jin L, Muldoon MJ, Ribeiro AP, Pombeiro AJ, Pârvulescu VI, Davey P, Hardacre C.
    Journal: Dalton Trans; 2017 Jan 31; 46(5):1704-1713. PubMed ID: 28102400.
    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.
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