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The Role of Symmetry in Asymmetric Catalysis
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2012 (English)In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 52, no 7, 653-662 p.Article, review/survey (Refereed) Published
Abstract [en]

Chiral ligands and metal complexes with rotational (Cn, Dn) symmetry often have beneficial properties in asymmetric catalysis. The enhanced enantioselectivity frequently observed is a result of a reduction of competing reaction routes. This may be due to rotational symmetry in the catalyst, leading to a limited number of different catalyst-substrate interactions, or to formation of a limited number of catalytic species as a result of rotational symmetry in the ligand. The effect of symmetry is usually difficult to evaluate, since a change in symmetry properties necessarily is accompanied by structural modifications. In each situation the number of intermediate complexes, their electronic and steric properties, and their energy need to be analyzed. Although other factors may be more important than symmetry for achieving high enantioselectivity, a vast number of C2- and to some extent C3-symmetric ligands have been found to have excellent properties in asymmetric catalysis, providing products with high enantiomeric purity. Besides the benefit of symmetry in the ligand and catalyst, the symmetry of the substrate may be important since a gain in enantioselectivity can result from simultaneous asymmetric transformations of homotopic functional groups.

Place, publisher, year, edition, pages
2012. Vol. 52, no 7, 653-662 p.
Keyword [en]
catalysis, enantioselectivity, homotopicity, paddlewheel, symmetry
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-100788DOI: 10.1002/ijch.201200020ISI: 000306510700010ScopusID: 2-s2.0-84864256627OAI: diva2:545087
QC 20120817Available from: 2012-08-17 Created: 2012-08-17 Last updated: 2012-08-17Bibliographically approved

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