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Convenient, Bismuth Mediated, One-pot, Two Component Synthesis of 2,6-Disubstituted-3,4-Dihydropyrans
Lambert, Robert Frederick
Lambert, Robert Frederick
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.
Description
Thesis is part of Honors ETD pilot project, 2008-2013. Migrated from Dspace in 2016.
Date
2011-05-09
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Keywords
Organic Chemistry, Bismuth, Dihydropyran
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Department
Chemistry