Premium
Substrate‐Controlled Product Divergence: Conversion of CO 2 into Heterocyclic Products
Author(s) -
Rintjema Jeroen,
Epping Roel,
Fiorani Giulia,
Martín Eddy,
EscuderoAdán Eduardo C.,
Kleij Arjan W.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511521
Subject(s) - nucleophile , intramolecular force , chemistry , amine gas treating , substrate (aquarium) , ring (chemistry) , alcohol , combinatorial chemistry , epoxy , stereochemistry , organic chemistry , medicinal chemistry , catalysis , oceanography , geology
Abstract Substituted epoxy alcohols and amines allow substrate‐controlled conversion of CO 2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO 2 ‐derived products by initial activation of CO 2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile‐assisted ring‐opening step following an S N i pathway, and a 5‐exo‐tet cyclization, thus leading to heterocyclic scaffolds.