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Title:Enantioenriched Homoaldol Products, Beta-Substituted Ketones, Isoxazolines, and Beta-Lactams Through Elaboration of Allylamine Asymmetric Homoenolate Equivalents: Synthesis and Elucidation of Reaction Pathways
Author(s):Whisler, Marna Christine
Doctoral Committee Chair(s):Beak, Peter
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:A stereocontrolled intramolecular nitrone/olefin dipolar cycloaddition reaction of enantioenriched enals provides cyclopentyl isoxazoline products in 64--81% yields and with diastereomeric ratios of 78:22 to 84:16. An isoxazoline was converted into an enantiomerically pure beta-lactam via a beta-amino alcohol and a beta-amino acid in six synthetic steps in 25% overall yield.
Issue Date:2002
Type:Text
Language:English
Description:226 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2002.
URI:http://hdl.handle.net/2142/84092
Other Identifier(s):(MiAaPQ)AAI3070472
Date Available in IDEALS:2015-09-25
Date Deposited:2002


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