An Enantioselective Inverse‐Electron‐Demand Imino Diels–Alder Reaction1. Issue 8 (27th January 2014)

• Record Type: Journal Article
• Authors: Eschenbrenner‐Lux, Vincent; Küchler, Philipp; Ziegler, Slava; Kumar, Kamal; Waldmann, Herbert
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 8(2014)
• Page Start: 2134
• Page End: 2137
• Publication Date: 2014-01-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201309022
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The imino Diels–Alder reaction is an efficient method for the synthesis of aza‐heterocycles. While different stereo‐ and enantioselective inverse‐electron‐demand imino Diels–Alder (IEDIDA) reactions have been reported before, IEDIDA reactions including electron‐deficient dienes are unprecedented. The first enantioselective IEDIDA reaction between electron‐poor chromone dienes and cyclic imines, catalyzed by zinc/binol complexes is described. The novel reaction provides a facile entry to a natural product inspired collection of ring‐fused quinolizines including a potent modulator of mitosis.</p> </abstract>