4.8 Article

The Prins Reaction Using Ketones: Rationalization and Application toward the Synthesis of the Portentol Skeleton

Journal

ORGANIC LETTERS
Volume 14, Issue 1, Pages 58-61

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202829u

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Funding

  1. Rennes Metropole
  2. Region Bretagne
  3. Universite de Rennes 1
  4. Ministere de la Recherche

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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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