Gold Catalyzed Cyclizations to form Oxygen Heterocycles
Research Mentor(s)
Vyvyan, James R.
Description
Gold catalysis has emerged over the past decade as an important methodology in the construction of organic molecules. Cationic gold complexes are robust, versatile, selective and efficient catalysts that can be used to enhance the electrophilicity of C-C unsaturated bonds. A current area of investigation is the use of gold to activate allylic alcohol/ether moieties for intramolecular SN2’ nucleophilic attack to form oxygen heterocycles. We have discovered that that sterically bulky, electron-withdrawing oxygen leaving groups drastically improved reaction efficiency and that bulky leaving groups and substrate substituents enhanced diastereomeric ratios in the oxygen heterocycle products. These reactions performed smoothly in the presence of many functional groups to consistently afford diastereoselective products.
Document Type
Event
Start Date
14-5-2015 10:00 AM
End Date
14-5-2015 2:00 PM
Department
Chemistry
Genre/Form
student projects; posters
Subjects – Topical (LCSH)
Gold; Organogold compounds; Oxygen; Homogeneous catalysis
Type
Image
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this documentation for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
Language
English
Format
application/pdf
Gold Catalyzed Cyclizations to form Oxygen Heterocycles
Gold catalysis has emerged over the past decade as an important methodology in the construction of organic molecules. Cationic gold complexes are robust, versatile, selective and efficient catalysts that can be used to enhance the electrophilicity of C-C unsaturated bonds. A current area of investigation is the use of gold to activate allylic alcohol/ether moieties for intramolecular SN2’ nucleophilic attack to form oxygen heterocycles. We have discovered that that sterically bulky, electron-withdrawing oxygen leaving groups drastically improved reaction efficiency and that bulky leaving groups and substrate substituents enhanced diastereomeric ratios in the oxygen heterocycle products. These reactions performed smoothly in the presence of many functional groups to consistently afford diastereoselective products.