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Literature DB >> 17465561

Gold-catalyzed efficient preparation of linear alpha-iodoenones from propargylic acetates.

Abstract

Only 2 mol % of Au(PPh3)NTf2 is needed to convert readily accessible propargylic acetates into versatile linear alpha-iodoenones in good to excellent yields. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of aliphatic propargylic acetates derived from aldehydes.

Entities: Chemical Gene

Year: 2007 PMID： 17465561 DOI： 10.1021/ol070637o

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

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Cited

18 in total

1. Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.

Authors: Hao Li; Ross A Widenhoefer
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

Review 2. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors: Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2011-01-24 Impact factor: 15.336

3. Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors: Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal: Angew Chem Int Ed Engl Date: 2018-05-07 Impact factor: 15.336

4. Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.

Authors: Biao Lu; Chaoqun Li; Liming Zhang
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

Gold-catalyzed efficient preparation of linear alpha-iodoenones from propargylic acetates.

1. Intramolecular Diamination and Alkoxyamination of Alkenes with N-Sulfonyl Ureas With N-Iodosuccinimide.

Review 2. Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

3. Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

4. Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.

5. Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.

6. Regio- and stereoselective synthesis of fluoroalkenes by directed Au(I) catalysis.

7. Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

8. Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

9. Complex alpha-pyrones synthesized by a gold-catalyzed coupling reaction.

10. Triazole-Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements.