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Literature DB >> 19449896

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

Barry M Trost¹, Alicia C Gutierrez, Robert C Livingston.

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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Year: 2009 PMID： 19449896 PMCID： PMC2728751 DOI： 10.1021/ol9007876

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

Review 1. Non-metathesis ruthenium-catalyzed C-C bond formation.

Authors: B M Trost; F D Toste; A B Pinkerton
Journal: Chem Rev Date: 2001-07 Impact factor: 60.622

2. Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex.

Authors: Zhou Xu; Jincheng Mao; Yawen Zhang
Journal: Org Biomol Chem Date: 2008-02-22 Impact factor: 3.876

3. A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans.

Authors: Barry M Trost; Hanbiao Yang; Georg Wuitschik
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

Review 4. Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors: L Pu; H B Yu
Journal: Chem Rev Date: 2001-03 Impact factor: 60.622

5. Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.

Authors: Ying Kit Chung; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.

Authors: Barry M Trost; Robert C Livingston
Journal: J Am Chem Soc Date: 2008-08-15 Impact factor: 15.419

7. Coupling of alkenes and alkynes: synthesis of the C1-C11 And C18-C28 fragments of miyakolide.

Authors: Barry M Trost; Brandon L Ashfeld
Journal: Org Lett Date: 2008-04-22 Impact factor: 6.005

8. Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.

Authors: Fei Yang; Peihua Xi; Li Yang; Jingbo Lan; Rugang Xie; Jingsong You
Journal: J Org Chem Date: 2007-06-08 Impact factor: 4.354

9. Si-based benzylic 1,4-rearrangement/cyclization reaction.

Authors: Barry M Trost; Andreas Bertogg
Journal: Org Lett Date: 2009-02-05 Impact factor: 6.005

10. Brønsted Acid-promoted intramolecular carbocyclization of alkynals leading to cyclic enones.

Authors: Carlos González-Rodríguez; Luz Escalante; Jesús A Varela; Luis Castedo; Carlos Saá
Journal: Org Lett Date: 2009-04-02 Impact factor: 6.005

7 in total

1. Triptycene diols: a strategy for synthesizing planar π systems through catalytic conversion of a poly(p-phenylene ethynylene) into a poly(p-phenylene vinylene).

Authors: Brett VanVeller; Dale Robinson; Timothy M Swager
Journal: Angew Chem Int Ed Engl Date: 2011-12-23 Impact factor: 15.336

2. Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N.

Authors: Barry M Trost; Jullien Rey
Journal: Org Lett Date: 2012-10-25 Impact factor: 6.005

3. Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael-Hemiacetalization Reaction.

Authors: Gregor Urbanietz; Iuliana Atodiresei; Dieter Enders
Journal: Synthesis (Stuttg) Date: 2014-05-01 Impact factor: 3.157