Zuschrift
Asymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones†
Adrian B. Pritzius,
Prof. Dr. Bernhard Breit,
Adrian B. Pritzius
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Bernhard Breit
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)Search for more papers by this authorAdrian B. Pritzius,
Prof. Dr. Bernhard Breit,
Adrian B. Pritzius
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Bernhard Breit
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany)Search for more papers by this author†
This work was supported by the DFG, the International Research, Training Group “Catalysts and Catalytic Reactions for Organic, Synthesis” (IRTG 1038), the Fonds der Chemischen Industrie, and the Krupp Foundation. We thank Umicore, BASF, and Wacker for generous gifts of chemicals. Ina Rohleff is acknowledged for skillful technical assistance.
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.
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