- 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
PMID22128826
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.
MATERIALS