2009•Organic LettersOpen access

A Novel Prins Cyclization through Benzylic/Allylic C−H Activation

Binxun Yu, Tuo Jiang, Junpeng Li, Yingpeng Su, Xinfu Pan, Xuegong She

Abstract

A step-economic method to construct the tetrahydropyran ring, involving sequential benzylic/allylic C-H bond activation via DDQ oxidation and nucleophilic attack of an unactivated olefin, is described. The equatorial-trisubstituted Prins products are obtained from benzyl and allyl homoallylic ethers with high yield and stereochemical fidelity.

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Key concepts: Allylic rearrangement, Chemistry, Tetrahydropyran, Prins reaction, Yield (engineering), Olefin fiber, Nucleophile, Ring (chemistry)