Journal
ORGANIC LETTERS
Volume 24, Issue 23, Pages 4275-4280Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01627
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Funding
- NIH [R35GM142965]
- North Carolina State University Faculty Research and Professional Development Program (FRPD)
- State of North Carolina
- NC State University
- NC State University's Office of Undergraduate Research
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This study reports a method for synthesizing particularly hindered tertiary alcohols via rearrangement reactions using [3,3]-sigmatropic rearrangements. Experimental studies suggest that the reaction proceeds through a close radical pair, leading to highly selective rearranged products.
Pericyclic processes such as [3,3]-sigmatropic rearrangements leading to the rapid generation of molecular complexity constitute highly valuable tools in organic synthesis. Herein, we report the formation of particularly hindered tertiary alcohols via rearrangement of Breslow intermediates formed in situ from readily available N-allyl thiazolium salts and benzaldehyde derivatives. Experimental mechanistic studies performed suggest that the reaction proceeds via a close radical pair which recombine in a regioand diastereoselective manner, formally leading to [3,3]-rearranged products.
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