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Convenient, Bismuth Mediated, One-pot, Two Component Synthesis of 2,6-Disubstituted-3,4-Dihydropyrans

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Author: Lambert, Robert Frederick
Advisor: Hinkle, Robert J.
Committee Members: Landino, Lisa M.; Galambush, Julie
Issued Date: 5/9/2011
Subjects: Organic Chemistry
Bismuth
Dihydropyran
URI: http://hdl.handle.net/10288/13675
Description: 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.
Degree: Bachelors of Science in Chemistry


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