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Tandem One‐Pot Approach to N ‐Substituted Lactones by Carbon–Carbon Coupling Followed by 5‐ exo ‐dig or 6‐ endo ‐dig Cyclization: DFT Studies and Cyclization Mode
Author(s) -
Mayooufi Atef,
Jacquemin Johan,
Petrignet Julien,
Thibonnet Jérôme
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901099
Subject(s) - dig , chemistry , sonogashira coupling , regioselectivity , tandem , intramolecular force , ring (chemistry) , stereochemistry , substituent , cascade reaction , medicinal chemistry , organic chemistry , palladium , catalysis , materials science , computer security , computer science , composite material
A one‐pot approach has been developed for the preparation of a five or six‐membered ring of unsaturated lactones bearing an amino group through a tandem coupling oxacyclization reaction. This tandem process involves Sonogashira‐like cross‐coupling followed by 5‐ exo ‐dig or 6‐ endo ‐dig intramolecular oxacyclization, according to the nature of the alkynes substituent. Furthermore, DFT calculations were performed to analyze the origin of this regioselectivity of cyclization.