Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven‐Membered‐Ring Oxocarbenium‐Ion Intermediates | Zendy

Beaver Matthew G. | Zendy; Buscagan Trixia M. | Zendy; Lavinda Olga | Zendy; Woerpel K. A. | Zendy

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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 , ring (chemistry) , chemistry , ion , stereochemistry , computational chemistry , organic chemistry , catalysis , nucleophile

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.

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