Substrate‐Controlled Product Divergence: Conversion of CO 2  into Heterocyclic Products | Zendy

Rintjema Jeroen | Zendy; Epping Roel | Zendy; Fiorani Giulia | Zendy; Martín Eddy | Zendy; EscuderoAdán Eduardo C. | Zendy; Kleij Arjan W. | Zendy

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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

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.

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