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

Maiwenn Jacolot Mickael Jean Nicolas Levoin Pierre van de Weghe

Org Lett

Université de Rennes 1, UMR 6226, Sciences Chimiques de Rennes, Equipe PNSCM, UFR des Sciences Biologiques et Pharmaceutiques, 2 avenue du Prof Léon Bernard, F-35043 Rennes Cedex, France.

Published: January 2012

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.

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http://dx.doi.org/10.1021/ol202829uDOI Listing

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