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

Jacolot, Maiwenn
Jean, Mickael
Van De Weghe, Pierre
Levoin, Nicolas

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Publication date

January 2012

DOI

10.1021/ol202829u

Publisher

American Chemical Society (ACS)

Abstract

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

Abstract

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

Abstract

Extracted data

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