Asymmetric Disulfonimide‐Catalyzed Synthesis of δ‐Amino‐β‐Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions1. Issue 49 (27th October 2014)

• Record Type: Journal Article
• Authors: Wang, Qinggang; van Gemmeren, Manuel; List, Benjamin
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 49(2014)
• Page Start: 13592
• Page End: 13595
• Publication Date: 2014-10-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201407532
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An organocatalytic asymmetric synthesis of δ‐amino‐β‐ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama–Mannich reaction of readily available dioxinone‐derived silyloxydienes with N‐Boc‐protected imines, delivering products in excellent yields and enantioselectivities. The synthetic utility of this reaction is illustrated in various transformations, including a new CC bond‐forming reaction, which provide useful enantioenriched building blocks. The methodology is applied in a formal synthesis of (−)‐lasubin.</p> </abstract>