Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 1704-1713 |
| Number of pages | 10 |
| Journal | Dalton Transactions |
| Volume | 46 |
| Issue number | 5 |
| Early online date | 21 Dec 2016 |
| DOIs | |
| Publication status | Published - 07 Feb 2017 |
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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 journal › Article
TY - JOUR
T1 - Using chiral ionic liquid additives to enhance asymmetric induction in a Diels–Alder reaction
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.
PY - 2017/2/7
Y1 - 2017/2/7
N2 - 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.
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.
U2 - 10.1039/c6dt04572c
DO - 10.1039/c6dt04572c
M3 - Article
VL - 46
SP - 1704
EP - 1713
JO - Dalton transactions (Cambridge, England : 2003)
JF - Dalton transactions (Cambridge, England : 2003)
SN - 1477-9226
IS - 5
ER -