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Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

ABSTRACT: An atom-economical method for the convenient synthesis of tetrahydropyrans and tetrahydrofurans is reported. Enones and enals derived from the [IndRu(PPh(3))(2)Cl]-catalyzed redox isomerization of primary and secondary propargyl alcohols undergo a subsequent intramolecular conjugate addition to provide cyclic ethers in excellent yields.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2728751 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

Trost Barry M BM Gutierrez Alicia C AC Livingston Robert C RC

Organic letters 20090601 12

An atom-economical method for the convenient synthesis of tetrahydropyrans and tetrahydrofurans is reported. Enones and enals derived from the [IndRu(PPh(3))(2)Cl]-catalyzed redox isomerization of primary and secondary propargyl alcohols undergo a subsequent intramolecular conjugate addition to provide cyclic ethers in excellent yields. ...[more]

PMID: 19449896

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