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Quan, Xu
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Publications (2 of 2) Show all publications
Verendel, J. J., Li, J.-Q., Quan, X., Peters, B., Zhou, T., Gautun, O. R., . . . Andersson, P. G. (2012). Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes. Chemistry - A European Journal, 18(21), 6507-6513
Open this publication in new window or tab >>Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes
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2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 21, p. 6507-6513Article in journal (Refereed) Published
Abstract [en]

Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates.

Keywords
asymmetric synthesis, heterocyclic compounds, homogeneous catalysis, hydrogenation, iridium
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-175620 (URN)10.1002/chem.201104073 (DOI)000304045000016 ()
Available from: 2012-06-12 Created: 2012-06-11 Last updated: 2017-12-07Bibliographically approved
Li, J.-Q., Xu, Q. & Andersson, P. (2012). Highly Enantioselective Iridium-Catalyzed Hydrogenation of α,β-Unsaturated Esters. Chemistry - A European Journal, 18(34), 10609-10616
Open this publication in new window or tab >>Highly Enantioselective Iridium-Catalyzed Hydrogenation of α,β-Unsaturated Esters
2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 34, p. 10609-10616Article in journal (Refereed) Published
Abstract [en]

α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-182641 (URN)10.1002/chem.201200907 (DOI)000307387300020 ()22807347 (PubMedID)
Available from: 2012-10-14 Created: 2012-10-14 Last updated: 2017-12-07Bibliographically approved
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