Using chiral ionic liquid additives to enhance asymmetric induction in a Diels-Alder reaction.

Autor: Goodrich P; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk., Nimal Gunaratne HQ; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk., Hall L; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk., Wang Y; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk., Jin L; School of Science, China Pharmaceutical University, Nanjing, 210009, P. R. China., Muldoon MJ; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk., Ribeiro AP; Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal., Pombeiro AJ; Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal., Pârvulescu VI; University of Bucharest, Department of Chemical Technology and Catalysis, B-dul Regina Elisabeta 4-12, Bucharest 030016, Romania., Davey P; Givaudan, Schweiz AG, Überlandstrasse 138, CH-8600 Dübendorf, Switzerland., Hardacre C; School of Chemistry and Chemical Engineering/QUILL, Queen's University, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK. p.goodrich@qub.ac.uk m.j.muldoon@qub.ac.uk and School of Chemical Engineering and Analytical Science, The University of Manchester, Sackville Street, Manchester, M13 9PL, UK. c.hardacre@manchester.ac.uk.
Jazyk: angličtina
Zdroj: Dalton transactions (Cambridge, England : 2003) [Dalton Trans] 2017 Jan 31; Vol. 46 (5), pp. 1704-1713.
DOI: 10.1039/c6dt04572c
Abstrakt: 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.
Databáze: MEDLINE