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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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