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DOI: 10.1055/s-0036-1588662
Perspectives on Intermolecular Azomethine Ylide [3+2] Cycloadditions with Non-Electrophilic Olefins
Publication History
Received: 26 September 2016
Accepted after revision: 02 November 2016
Publication Date:
15 December 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201704/lookinside/thumbnails/ss-2016-z0671-sr_10-1055_s-0036-1588662-1.jpg)
‡ The authors contributed equally.
Dedicated to Prof. Paul Knochel.
Abstract
Our interest in the synthesis of compact nitrogen heterocycles from abundant sources has motivated a critical analysis of the status in azomethine ylide chemistry. Despite the outstanding developments in catalytic enantioselective [3+2] cycloadditions, these are still limited to electron-poor olefins. Only a few examples can be found in the literature that report on cycloadditions using non-electrophilic alkenes and those are compiled herein. With this account we aim to extract lessons and challenges that will inspire future breakthroughs in this area.
1 Introduction
2 State-of-the-Art Using Electron-Poor Olefins
3 Research on Activated Non-Electrophilic Olefins
3.1 Aromatic Olefins
3.2 Polyenes
3.3 Hetero-Substituted Olefins
3.4 Rare Examples with Alkyl-Substituted Olefins: Norbornadiene and Tethered α-Olefins
4 Extracted Generalities
4.1 Kinetic Barrier to Non-Electrophilic Olefins
4.2 Charge Concentration: An Unsolved Thermodynamic Penalty
5 Conclusions and Outlook
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