Date Thesis Awarded
Honors Thesis -- Open Access
Bachelors of Science (BS)
Robert J. Hinkle
Lisa M. Landino
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.
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.
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