title: Rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes.
abstract: A rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes to give branched N-allyl 2-pyridones is reported. Preliminary mechanistic studies support the hypothesis that the reaction was initiated from the more acidic 2-hydroxypyridine form, and the initial kinetic O-allylation product was finally converted into the thermodynamically more stable N-allyl 2-pyridones.
authors.affiliation: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany) http://portal.uni-freiburg.de/oc-breit.
authors.forename: Changkun
authors.initials: C
authors.lastname: Li
authors.forename: Matthias
authors.initials: M
authors.lastname: Kähny
authors.forename: Bernhard
authors.initials: B
authors.lastname: Breit
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D011728:Pyridones / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D011728:Pyridones; C025947:propadiene; C017679:2-hydroxypyridine; D012238:Rhodium
keywords: 2-pyridones; allenes; asymmetric allylation; reaction mechanisms; rhodium