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Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven‐Membered‐Ring Oxocarbenium‐Ion Intermediates
Author(s) -
Beaver Matthew G.,
Buscagan Trixia M.,
Lavinda Olga,
Woerpel K. A.
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.201507806
Subject(s) - oxocarbenium , stereoselectivity , chemistry , nucleophile , ring (chemistry) , stereochemistry , ion , nucleophilic addition , organic chemistry , catalysis
Nucleophilic attack on seven‐membered‐ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six‐membered‐ring oxocarbenium ions.