Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)‐Catalyzed C−H Alkylation of Azacycles. Issue 35 (24th July 2017)

• Record Type: Journal Article
• Authors: Tran, Anh T.; Yu, Jin‐Quan
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 35(2017)
• Page Start: 10530
• Page End: 10534
• Publication Date: 2017-07-24
• Subjects: alkylation -- C−H activation -- homogeneous catalysis -- N-heterocycles -- pentoxythiocarbonyl; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201704755
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The development of new and practical 3‐pentoxythiocarbonyl auxiliaries for Ir I ‐catalyzed C−H alkylation of azacycles is described. This method allows for the α‐C−H alkylation of a variety of substituted pyrrolidines, piperidines, and tetrahydroisoquinolines through alkylation with alkenes. While the practicality of these simple carbamate‐type auxiliaries is underscored by the ease of installation and removal, the method's utility is demonstrated in its ability to functionalize biologically relevantl ‐proline andl ‐ trans ‐hydroxyproline, delivering unique 2, 5‐dialkylated amino acid analogues that are not accessible by other C−H functionalization methods. Abstract : Fine‐tuning : A carbamate‐type 3‐pentoxythiocarbonyl auxiliary has been developed for the α‐C−H alkylation of a variety of substituted N‐heterocycles through reaction with alkenes (see scheme). Application to biologically relevantl ‐proline andl ‐ trans ‐hydroxyproline delivered unique 2, 5‐dialkylated amino acid analogues.