title: Asymmetric rhodium-catalyzed addition of thiols to allenes: synthesis of branched allylic thioethers and sulfones.
abstract: A highly regio- and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form. The reaction tolerates a variety of functional groups and labeling experiments gave first insights into the reaction mechanism of this new methodology.
authors.affiliation: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany).
authors.forename: Adrian B
authors.initials: AB
authors.lastname: Pritzius
authors.forename: Bernhard
authors.initials: B
authors.lastname: Breit
keywords: asymmetric catalysis; enantioselectivity; ethers; rhodium; sulfur