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Asymmetric nucleophilic catalysis with planar-chiral DMAP derivatives and chiral phosphines : synthetic and mechanistic studies

Author(s)
Lee, Sarah Yunmi
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Massachusetts Institute of Technology. Department of Chemistry.
Advisor
Gregory C. Fu.
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M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582
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Abstract
Chapter 1 describes the development and detailed mechanistic investigation of the first non-enzymatic method for the dynamic kinetic resolution of secondary alcohols via enantioselective acylation, with acetyl isopropyl carbonate, through the use of a planar-chiral DMAP derivative (an acylation catalyst) in combination with a ruthenium complex (an alcohol-racemization catalyst). Chapter 2 describes the development and detailed mechanistic investigation of the enantioselective synthesis of tertiary alkyl fluorides via the [alpha]-fluorination of ketenes catalyzed by a planar-chiral nucleophile with N-fluorodibenzenesulfonimide in the presence of sodium pentafluorophenoxide. Chapter 3 describes the development and preliminary mechanistic study of the first asymmetric, phosphine-catalyzed intramolecular [3 + 2] cycloadditions of allenes with alkenes that furnish an array of diastereomerically pure bicyclic compounds bearing two or three contiguous tertiary! quaternary stereocenters.
Description
Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2014.
 
Cataloged from PDF version of thesis. Vita.
 
Includes bibliographical references.
 
Date issued
2014
URI
http://hdl.handle.net/1721.1/93035
Department
Massachusetts Institute of Technology. Department of Chemistry
Publisher
Massachusetts Institute of Technology
Keywords
Chemistry.

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