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

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

Organic letters (2011-12-02)
Maiwenn Jacolot, Mickael Jean, Nicolas Levoin, Pierre van de Weghe
초록

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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Sigma-Aldrich
1-(Trimethylsilyl)imidazole, 96%