2009Unpublished venueRequires access

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

俞斌勋, 蒋拓, 李俊鹏, 苏瀛鹏, Pan Xin Fu, 厍学功

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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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What this paper is about

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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Available 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.

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

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