Persistent Link:
http://hdl.handle.net/10150/144597
Title:
New Nucleophilic Organocatalysts
Author:
Harris, David T.
Issue Date:
2011
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Acyl-transfer reactions have become commonplace in organic synthesis and organocatalysis of these reactions is becoming increasingly popular. 4-Dimethylaminopyridine has proven to be very useful in acylations; over the recent years chiral and more reactive analogs have received much attention. Interestingly, catalysis of acyl-transfers by diamines has also been shown to be effective. We present the synthesis of several DMAP analogs containing heteroatoms near the nucleophilic nitrogen. These analogs of DMAP vary from basic amidines, oxazolines, and amines, to alcohols, and fluoro-derivatives all of which may provide hydrogen bonding to the alcohol undergoing acyl-transfer. Since Steglich proposed the need for a base in the DMAP catalyzed acyl-transfer transition state no studies have been performed on the effect that nearby hydrogen bonding or nearby bases might have on catalytic efficiency and enantioselectivity of acylations. The variety of compounds synthesized should allow for studies into rate and selectivity enhancements in nucleophilic pyridine catalysis.
Type:
Electronic Thesis; text
Keywords:
dialkylamino; nucleophilic; organocatalyst; pyridine
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Christie, Hamish S

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleNew Nucleophilic Organocatalystsen_US
dc.creatorHarris, David T.en_US
dc.contributor.authorHarris, David T.en_US
dc.date.issued2011-
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractAcyl-transfer reactions have become commonplace in organic synthesis and organocatalysis of these reactions is becoming increasingly popular. 4-Dimethylaminopyridine has proven to be very useful in acylations; over the recent years chiral and more reactive analogs have received much attention. Interestingly, catalysis of acyl-transfers by diamines has also been shown to be effective. We present the synthesis of several DMAP analogs containing heteroatoms near the nucleophilic nitrogen. These analogs of DMAP vary from basic amidines, oxazolines, and amines, to alcohols, and fluoro-derivatives all of which may provide hydrogen bonding to the alcohol undergoing acyl-transfer. Since Steglich proposed the need for a base in the DMAP catalyzed acyl-transfer transition state no studies have been performed on the effect that nearby hydrogen bonding or nearby bases might have on catalytic efficiency and enantioselectivity of acylations. The variety of compounds synthesized should allow for studies into rate and selectivity enhancements in nucleophilic pyridine catalysis.en_US
dc.typeElectronic Thesisen_US
dc.typetexten_US
dc.subjectdialkylaminoen_US
dc.subjectnucleophilicen_US
dc.subjectorganocatalysten_US
dc.subjectpyridineen_US
thesis.degree.nameM.S.en_US
thesis.degree.levelmastersen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorChristie, Hamish Sen_US
dc.contributor.committeememberPolt, Robin Len_US
dc.contributor.committeememberGlass, Richard Sen_US
dc.identifier.proquest11625-
dc.identifier.oclc752261480-
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