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Article Dans Une Revue Organic Letters Année : 2012

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

Résumé

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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hal-00841525 , version 1 (05-07-2013)

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Maiwenn Jacolot, Mickael Jean, Pierre van de Weghe, Nicolas Levoin. The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.. Organic Letters, 2012, 14 (1), pp.58-61. ⟨10.1021/ol202829u⟩. ⟨hal-00841525⟩
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