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Literature DB >> 16986932

Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols.

Abstract

The tandem cycloisomerization-hydroalkoxylation of various homopropargylic alcohols in the presence of an alcohol and a dual catalyst system, consisting of a gold precatalyst and a Brønsted acid, provides an efficient route to tetrahydrofuranyl ethers under mild reaction conditions. The reaction can be carried out in various solvents, including alcohol, with both terminal and internal alkynes as the substrate.

Entities: Chemical

Year: 2006 PMID： 16986932 DOI： 10.1021/ol061751u

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

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Cited

17 in total

1. Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol.

Authors: Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal: Org Lett Date: 2007-07-17 Impact factor: 6.005

2. Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors: David S Barnett; Scott E Schaus
Journal: Org Lett Date: 2011-07-06 Impact factor: 6.005

3. Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors: Megan K Armstrong; Gojko Lalic
Journal: J Am Chem Soc Date: 2019-04-03 Impact factor: 15.419

4. Gold catalyzed cyclization of alkyne-tethered dihydropyrimidones.

Authors: Lauren E Brown; Peng Dai; John A Porco; Scott E Schaus
Journal: Org Lett Date: 2011-07-13 Impact factor: 6.005

5. A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis.

Authors: Barry M Trost; Benjamin R Taft; James T Masters; Jean-Philip Lumb
Journal: J Am Chem Soc Date: 2011-05-16 Impact factor: 15.419

6. Enantioselective synthesis of alkyne-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution reactions with (i-Bu)2(alkynyl)aluminum reagents.

Authors: Jennifer A Dabrowski; Fang Gao; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-03-08 Impact factor: 15.419

7. Differential Dihydrofunctionalization: A Dual Catalytic Three-Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.

Authors: James E Baumann; Gojko Lalic
Journal: Angew Chem Int Ed Engl Date: 2022-08-03 Impact factor: 16.823