Back to results
University of Illinois at 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
Abstract
dc:descriptionA 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.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Whisler, Marna Christine
- Contributors dc:contributor
-
- Beak, Peter
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3070472
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84092