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Synthesis 2015; 47(23): 3813-3821
DOI: 10.1055/s-0034-1381058
DOI: 10.1055/s-0034-1381058
paper
Asymmetric Synthesis of Tetrahydropyridines via a Brønsted Acid Catalyzed Aza-Diels–Alder Reaction
Weitere Informationen
Publikationsverlauf
Received: 23. Juli 2015
Accepted: 27. Juli 2015
Publikationsdatum:
13. August 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201523/lookinside/thumbnails/ss-2015-z0454-op_10-1055_s-0034-1381058-1.jpg)
Abstract
The asymmetric synthesis of tetrahydropyridines employing a normal electron-demanding aza-Diels–Alder reaction has been developed. The [4+2] cycloaddition of ethyl glyoxylate imine with aryl-substituted 2-silyloxy-1,3-butadienes is catalyzed by 5 mol% of a BINOL-derived phosphoric acid and in general leads to good yields and ee values with good to excellent diastereoselectivities. The cycloadducts can be further converted into the corresponding piperidinones, which are important pipecolic acid derivatives.
Key words
aza-Diels–Alder reaction - asymmetric synthesis - Brønsted acid - organocatalysis - glyoxylate imineSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381058.
- Supporting Information
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