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Synthesis 2012; 44(18): 2947-2958
DOI: 10.1055/s-0032-1316751
DOI: 10.1055/s-0032-1316751
paper
An Imine-Based Route to Polycyclic Chlorinated ε-Lactams by Formation of C–C Bonds as Key Steps
Weitere Informationen
Publikationsverlauf
Received: 16. Mai 2012
Accepted after revision: 23. Juni 2012
Publikationsdatum:
30. Juli 2012 (online)
![](https://www.thieme-connect.de/media/synthesis/201218/lookinside/thumbnails/10.1055-s-0032-1316751-1.jpg)
Abstract
A two-step sequence for the conversion of heterocyclic imines to saturated and unsaturated polycyclic chlorinated ε-lactams is disclosed. In the first step, an acyl chloride addition followed by a substitution is used to achieve unsaturated methoxyamides. The final lactamization to two different classes of polycyclic ε-lactams via formation of a C–C bond is realized by the use of metal chlorides as Lewis acid and as a source of chloride. The potential of the ε-lactams in subsequent reactions is demonstrated by an elimination reaction.
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For excellent reviews dealing with multicomponent reactions, see:
For selected examples, see:
For selected examples, see:
For selected examples, see: