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Peters, Byron
Publications (3 of 3) 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
Zhou, T., Peters, B., Maldonado, M., Govender, T. & Andersson, P. (2012). Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds. Journal of the American Chemical Society, 134(33), 13592-13595
Open this publication in new window or tab >>Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds
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2012 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 134, no 33, p. 13592-13595Article in journal (Refereed) Published
Abstract [en]

A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Backlund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).

National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-182640 (URN)10.1021/ja306731u (DOI)000307699000016 ()
Available from: 2012-10-14 Created: 2012-10-14 Last updated: 2017-12-07Bibliographically approved
Li, J.-Q., Peters, B. & Andersson, P. G. (2011). Highly Enantioselective Asymmetric Isomerization of Primary Allylic Alcohols with an Iridium-N,P Complex. Chemistry - A European Journal, 17(40), 11143-11145
Open this publication in new window or tab >>Highly Enantioselective Asymmetric Isomerization of Primary Allylic Alcohols with an Iridium-N,P Complex
2011 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 40, p. 11143-11145Article in journal (Refereed) Published
Keywords
aldehydes, allylic alcohols, asymmetric catalysis, iridium, isomerization, N, P ligands
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-164577 (URN)10.1002/chem.201101524 (DOI)000297013100011 ()
Available from: 2011-12-21 Created: 2011-12-21 Last updated: 2017-12-08Bibliographically approved
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