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. 2009 Jun 18;11(12):2539-42.
doi: 10.1021/ol9007876.

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

Barry M Trost  1 , Alicia C Gutierrez, Robert C Livingston
Affiliations

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

Barry M Trost et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Tandem Redox-Isomerization–Conjugate Addition to Generate Cyclic Aldehydes
Scheme 2
Scheme 2
Facile Access to Cyclic Ethers
See this image and copyright information in PMC

References

    1. Reviews containing leading references in this area: Trost BM, Frederiksen MU, Rudd MT. Angew. Chem., Int. Ed. 2005;44:6630. Trost BM. Acc. Chem. Res. 2002;35:695. Trost BM, Toste FD, Pinkerton AB. Chem. Rev. 2001;101:2067. Recent advances: Trost BM, Bertogg A. Org. Lett. 2009;11:511. Trost BM, Ashfeld BL. Org. Lett. 2008;10:1893. Trost BM, Ferreira EM, Gutierrez AC. J. Am. Chem. Soc. 2008;130:16176. Trost BM, Xie J, Maulide N. J. Am. Chem. Soc. 2008;130:17258. Trost BM, Machacek MR, Faulk BD. J. Am. Chem. Soc. 2006;128:6745. Trost BM, McClory A. Org. Lett. 2006;8:3627. Trost BM, Huang X. Chem. Asian J. 2006;1:469.

    1. Stang PJ, Diederich F, editors. Modern Acetylene Chemistry. Weinheim, Germany: VCH; 1995.

    1. Examples of tetrahydropyran- and tetrahydrofuran-containing natural products include Bryostatin, Salinomcin, Latrunculin A, Spongistatin 1, Swinholide A, Hemibrevitoxin B, Glabrescol, Pamamycin 607, and Sclerophytin A.

    1. For reviews containing leading references on the development of methods for the synthesis of tetrahydropyrans, tetrahydrofurans, and oxepanes see: Piccialli V. Synthesis. 2007;17:2585. Elliot MC. J. Chem. Soc., Perkin. Trans. 2002;1:2301. Boivin TL. Tetrahedron. 1987;43:3309. Recent advances: Zhu H, Wickenden JG, Campbell NE, Leung JCT, Johnson KM, Sammis GM. Org. Lett. 2009;11:2019. Fu GC, Chung YK. Angew. Chem. Int. Ed. 2009;48:2225. Dzudza A, Marks T. Org. Lett. 2009;11:1523. Gonzlez-Rodrguez C, Escalante L, Varela JA, Castedo L, Saa C. Org. Lett. 2009;11:1531. Samanta S, Mohapatra H, Jana R, Ray JK. Tetrahedron Lett. 2008;49:7153. Kimishima A, Nakata T. Tetrahedron Lett. 2008;49:6563. Jamison TF, Vilotijevic I. Science. 2007;317:1189. Kartika R, Taylor RE. Angew. Chem. Int. Ed. 2007;46:6874. Yadav JS, Rajasekhar K, Murty MS. Synlett. 2005;12:1945. Trost BM, Yang H, Wuitschik G. Org. Lett. 2005;7:4761.

    1. Trost BM, Livingston RB. J. Am. Chem. Soc. 1995;117:9586.
    2. Trost BM, Livingston RB. J. Am. Chem. Soc. 2008;130:11970. - PMC - PubMed

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