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American Chemical Society, Organic Letters, 1(14), p. 58-61, 2011

DOI: 10.1021/ol202829u

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The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.

Journal article published in 2011 by Maiwenn Jacolot ORCID, Mickael Jean, Nicolas Levoin, Pierre Van De Weghe
This paper is available in a repository.
This paper is available in a repository.

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Abstract

We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.