Back to results
University of Illinois at Urbana-Champaign
Studies on the Total Synthesis of (+/-)-Cameroonan-7alpha-Ol and Presilphiperfolan-8-Ol and Discovery of a Novel Stereoselective Prins Cyclization of Delta,epsilon-Unsaturated Ketones
Abstract
dc:descriptionA novel stereoselective Prins cyclization reaction of unsaturated ketones was discovered. It was found that reaction of TiCl4 with delta,epsilon- or epsilon,zeta-unsaturated ketones at low temperature followed by buffered methanolysis provided monocyclic and bicyclic cis 3-chlorocyclohexanols. Testing of ten unsaturated ketones and four acid activators provided evidence for substrate generality while the stereoselectivity was rationalized by intramolecular delivery of the nucleophile.
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
-
- Davis, Chad Eric
- Contributors dc:contributor
-
- Coates, Robert M.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3086042
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84098