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Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

ABSTRACT: Oxidative activation of benzyl or cinnamyl ether bearing allylsilane derivatives using a catalytic amount of DDQ and 2 equivalents of CAN in the presence of PPTS provided functionalized 4-methylenetetrahydropyrans in good yields and excellent diastereoselectivity. The reaction could be applied to the synthesis of a variety of substituted tetrahydropyran derivatives.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC3388552 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

Ghosh Arun K AK Cheng Xu X

Tetrahedron letters 20120501 20

Oxidative activation of benzyl or cinnamyl ether bearing allylsilane derivatives using a catalytic amount of DDQ and 2 equivalents of CAN in the presence of PPTS provided functionalized 4-methylenetetrahydropyrans in good yields and excellent diastereoselectivity. The reaction could be applied to the synthesis of a variety of substituted tetrahydropyran derivatives. ...[more]

PMID: 22773862

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