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Literature DB >> 16967944

Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes.

Abstract

The gold(I)-catalyzed carboalkoxylation of alkynes to form indanone derivatives from readily available ortho-acetylenic benzylic ethers is described. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched benzylic ethers proceeds with chirality transfer, thus providing a practical method for the enantioselective synthesis of indenyl ethers.

Entities: Chemical

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Year: 2006 PMID： 16967944 DOI： 10.1021/ja064209+

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 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. Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors: Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2015-06-01 Impact factor: 15.336

3. Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors: Weiwei Zi; F Dean Toste
Journal: J Am Chem Soc Date: 2013-08-19 Impact factor: 15.419

4. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors: Nathan D Shapiro; F Dean Toste
Journal: Synlett Date: 2010-03-01 Impact factor: 2.454

5. Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.

Authors: Yi-Ming Wang; Christian N Kuzniewski; Vivek Rauniyar; Christina Hoong; F Dean Toste
Journal: J Am Chem Soc Date: 2011-07-28 Impact factor: 15.419

6. Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination.

Authors: William E Brenzovich; Diego Benitez; Aaron D Lackner; Hunter P Shunatona; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2010-07-26 Impact factor: 15.336

Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes.

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

2. Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

3. Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

4. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

5. Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.

6. Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination.

7. Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

8. Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Review 9. Ligand effects in homogeneous Au catalysis.

10. Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles.