Asymmetric Rhodium‐Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones1. (16th January 2015)

• Record Type: Journal Article
• Authors: Pritzius, Adrian B.; Breit, Bernhard
• Is Part Of: Angewandte Chemie. Volume 127:Number 10(2015)
• Page Start: 3164
• Page End: 3168
• Publication Date: 2015-01-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201411402
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>