Aza-Diels–Alder reaction
| Aza-Diels–Alder reaction | |
|---|---|
| Named after | Otto Diels Kurt Alder |
| Reaction type | Cycloaddition |
| Identifiers | |
| RSC ontology ID | RXNO:0000092 |
The aza-Diels–Alder reaction converts
dienophile
.
The imine is often generated in situ from an amine and formaldehyde. An example is the reaction of cyclopentadiene with benzylamine to an aza norbornene.[1]
In the
enantioselective Diels–Alder (DA) reaction of an aniline, formaldehyde and a cyclohexenone catalyzed by (S)-proline even the diene is masked.[2]
The
Si face
. Hydrolysis of the final complex releases the product and regenerates the catalyst.
In 2014, Doyle and coworkers reported a Zn(OTf)2-catalyzed [4+2] cycloaddition reaction between two imines to form tetrahydropyrimidine products.[3]
See also
- Oxo Diels–Alder reaction
- Imine Diels–Alder reaction
References
- ^ N-benzyl-2-azanorbornene Paul A. Grieco and Scott D. Larsen Organic Syntheses, Coll. Vol. 8, p.31; Vol. 68, p.206 Article
- Angewandte Chemie International Edition 4877 2005 Abstract
- ^ Mandler, M. D.; Truong, P. M.; Zavalij, P. Y.; Doyle, M. P. Org. Lett. 2014, 16, 740-743.