| Publication Type |
Journal Article |
| Title |
Using chiral ionic liquid additives to enhance asymmetric induction in a Diels-Alder reaction |
| Authors |
P. Goodrich H. Q. Nimal Gunaratne L. Hall Y. Wang L. Jin M. J. Muldoon A.P.C. Ribeiro Armando J.L. Pombeiro V. I. Parvulescu P. Davey C. Hardacre |
| Groups |
|
| Journal |
DALTON TRANSACTIONS |
| Year |
2017 |
| Month |
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|
| Volume |
46 |
| Number |
5 |
| Pages |
1704-1713 |
| 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. |
| DOI |
http://dx.doi.org/10.1039/c6dt04572c |
| ISBN |
|
| Publisher |
ROYAL SOC CHEMISTRY |
| Book Title |
|
| ISSN |
1477-9226 |
| EISSN |
1477-9234 |
| Conference Name |
|
| Bibtex ID |
ISI:000395442700040 |
| Observations |
|
