University of Illinois Urbana-Champaign

Enantioenriched Homoaldol Products, Beta-Substituted Ketones, Isoxazolines, and Beta-Lactams Through Elaboration of Allylamine Asymmetric Homoenolate Equivalents: Synthesis and Elucidation of Reaction Pathways

Whisler, Marna Christine

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Description

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
Issue Date
2002
Doctoral Committee Chair(s)
Beak, Peter
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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.
Graduation Semester
2002
Type of Resource
text
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http://hdl.handle.net/2142/84092

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