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- Title
Utility of 2‐Diphenylphosphoryloxy‐1,3‐Dienes in Multicomponent Hetero‐Diels–Alder Reactions to Construct Functionalized Six‐Membered Nitrogen Heterocycles.
- Authors
He, Qiuyu; Cao, Lirong; Wei, Yiran; Dake, Gregory R.
- Abstract
The utility of 2‐diphenylphosphoryloxy‐1,3‐dienes for the construction of substituted six‐membered nitrogen heterocycles is presented. These dienes undergo boron trifluoride‐promoted aza‐Diels–Alder reactions when reacted with imines or related species formed in situ using aldehydes and amine derivatives. The stability of the dienes allows this three‐component reaction to be carried out with no special precautions to eliminate water or air. Thirty‐one examples of this process are presented. The usefulness of the enol phosphate functional group is highlighted in further reactions after the cycloaddition step to generate functionalized piperidenes or pyridines.
- Subjects
HETEROCYCLIC compounds; ALDEHYDE derivatives; NITROGEN; AMINE derivatives; RING formation (Chemistry)
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 42, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202201328