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, Mark Muldoon, A. P. C. Ribeiro, A. J. L. Pombeiro, V. I. Pârvulescu, P. Davey, C. Hardacre

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)1704-1713
Number of pages10
JournalDalton Transactions
Volume46
Issue number5
Early online date21 Dec 2016
DOIs
Publication statusPublished - 07 Feb 2017

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Ionic Liquids
Catalysts
Enantioselectivity
Cyclopentanes
Biological Products
Ligands

Cite this

Goodrich, P. ; Gunaratne, H. Q. Nimal ; Hall, L. ; Wang, Y. ; Jin, L. ; Muldoon, Mark ; Ribeiro, A. P. C. ; Pombeiro, A. J. L. ; Pârvulescu, V. I. ; Davey, P. ; Hardacre, C. / Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction. In: Dalton Transactions. 2017 ; Vol. 46, No. 5. pp. 1704-1713.
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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.",
author = "P. Goodrich and Gunaratne, {H. Q. Nimal} and L. Hall and Y. Wang and L. Jin and Mark Muldoon and Ribeiro, {A. P. C.} and Pombeiro, {A. J. L.} and P{\^a}rvulescu, {V. I.} and P. Davey and C. Hardacre",
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Goodrich, P, Gunaratne, HQN, Hall, L, Wang, Y, Jin, L, Muldoon, M, Ribeiro, APC, Pombeiro, AJL, Pârvulescu, VI, Davey, P & Hardacre, C 2017, 'Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction', Dalton Transactions, vol. 46, no. 5, pp. 1704-1713. https://doi.org/10.1039/c6dt04572c

Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction. / Goodrich, P.; Gunaratne, H. Q. Nimal; Hall, L.; Wang, Y.; Jin, L.; Muldoon, Mark; Ribeiro, A. P. C.; Pombeiro, A. J. L.; Pârvulescu, V. I.; Davey, P.; Hardacre, C.

In: Dalton Transactions, Vol. 46, No. 5, 07.02.2017, p. 1704-1713.

Research output: Contribution to journalArticle

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AU - Goodrich, P.

AU - Gunaratne, H. Q. Nimal

AU - Hall, L.

AU - Wang, Y.

AU - Jin, L.

AU - Muldoon, Mark

AU - Ribeiro, A. P. C.

AU - Pombeiro, A. J. L.

AU - Pârvulescu, V. I.

AU - Davey, P.

AU - Hardacre, C.

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Y1 - 2017/2/7

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AB - 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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