Copper‐Catalyzed Cyclization/aza‐Claisen Rearrangement Cascade Initiated by Ketenimine Formation: An Efficient Stereocontrolled Synthesis of α‐Allyl Cyclic Amidines1. Issue 35 (2nd July 2014)

• Record Type: Journal Article
• Authors: Xu, Hua‐Dong; Jia, Zhi‐Hong; Xu, Ke; Han, Mei; Jiang, Sai‐Nan; Cao, Jing; Wang, Jia‐Cheng; Shen, Mei‐Hua
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 35(2014)
• Page Start: 9284
• Page End: 9288
• Publication Date: 2014-07-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405331
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An efficient and convenient synthesis of α‐allyl cyclic amidines has been achieved by applying a novel cascade reaction. Copper(I)‐mediated in situ N‐sulfonyl ketenimine formation from the reaction of a terminal alkyne with sulfonyl azide is followed by an intramolecular nucleophilic attack on the central carbon atom by an allylic tertiary amine, and then an aza‐Claisen rearrangement takes place through a chair transition state to furnish the titled amidines with complete stereocontrol.</p> </abstract>