Nickel-Catalyzed Alkene Isomerization to Access Bench-Stable Enamines and Their [3 + 2] Annulation.
J Org Chem
; 89(13): 9233-9242, 2024 Jul 05.
Article
in En
| MEDLINE
| ID: mdl-38912727
ABSTRACT
Enamines are difficult to prepare on the bench due to their instability, which results in side reactions, decompositions, poor yields, etc. Herein, we developed a simple and effective method for making bench-stable enamines using a very low amount of nickel catalyst loading. The deuterium exchange, competitive reaction, and radical clock experiment have all been found to favor the ionic mechanism of this alkene isomerization. Scale-up and [3 + 2] annulation reaction of enamines with activated cyclopropane to deliver cyclopentane derivatives have shown the value of this method in organic synthesis.
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1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
/
J. org. chem
/
Journal of organic chemistry
Year:
2024
Document type:
Article
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