Intramolecular oxa-Michael and Baylis Hillman Strategies towards Sultam Libraries
Issue Date
2011-05-31Author
Knudtson, Christopher Anton
Publisher
University of Kansas
Format
91 pages
Type
Thesis
Degree Level
M.S.
Discipline
Chemistry
Rights
This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
Metadata
Show full item recordAbstract
The utilization of Baylis-Hillman and oxa-Michael methodologies for the synthesis of sultam (cyclic sulfonamides) libraries from chiral non-racemic amino alcohols and epoxides is reported. These strategies employ a divergent synthetic approach utilizing a central vinyl sulfonamide linchpin and a variety of functional group pairing reactions to generate skeletally diverse sultam scaffolds with a variety of functionalizable handles. A variety of 5, 6, 7, and 8-member sultams are accessible through these methods with excellent diastereoselectivity, yields, and purities. In addition, the oxa-Michael protocol has been utilized in a one-pot protocol for the synthesis of alibrary of 4,4-dioxo-1,4,5-oxathiazepines.
Collections
- Chemistry Dissertations and Theses [335]
- Theses [3940]
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.