Date Thesis Awarded
5-2011
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Robert J. Hinkle
Committee Members
Lisa M. Landino
Julie Galambush
Abstract
The synthesis of cis-2,6-dihydropyrans is successfully accomplished through tandem Intramolecular silyl-Modified Sakurai (ISMS)/silyl-Prins type reaction, mediated by Bi(OTf)3. A variety of epoxides and vinyl silanols prove effective in providing cis-2,6-dihydropyrans in moderate to good yield and excellent diasterioselectivities. Scope, limitations, and mechanistic considerations of the protocol are described herein.Additionally, within the development of this methodology, the catalytic process involving Bi(X)3 salts was investigated.
Recommended Citation
Lambert, Robert Frederick, "Convenient, Bismuth Mediated, One-pot, Two Component Synthesis of 2,6-Disubstituted-3,4-Dihydropyrans" (2011). Undergraduate Honors Theses. William & Mary. Paper 371.
https://scholarworks.wm.edu/honorstheses/371
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Comments
Thesis is part of Honors ETD pilot project, 2008-2013. Migrated from Dspace in 2016.