Literature DB >> 16928065

Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement.

Douglas A Engel1, Gregory B Dudley.   

Abstract

An atom-economical and efficient olefination strategy for ketones is described. Ethoxyacetylide addition followed by a gold-catalyzed Meyer-Schuster rearrangement affords alpha,beta-unsaturated esters, generally in excellent overall yield from the starting ketones. The alkynophilicity of Au3+ promotes an interaction with the electron-rich acetylenes that catalyzes the Meyer-Schuster rearrangement selectively over other conceivable pathways.

Entities:  

Year:  2006        PMID： 16928065     DOI： 10.1021/ol0616743

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


  10 in total

1.  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

2.  Gold-Catalyzed Oxidation of Propargylic Ethers with Internal C-C Triple Bonds: Impressive Regioselectivity Enabled by Inductive Effect.

Authors:  Kegong Ji; Brendan D'Souza; Jon Nelson; Liming Zhang
Journal:  J Organomet Chem       Date:  2014-11-01       Impact factor: 2.369

3.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157

4.  Gold-catalyzed propargylic substitutions: Scope and synthetic developments.

Authors:  Olivier Debleds; Eric Gayon; Emmanuel Vrancken; Jean-Marc Campagne
Journal:  Beilstein J Org Chem       Date:  2011-06-28       Impact factor: 2.883

5.  Regioselective dihalohydration reactions of propargylic alcohols: gold-catalyzed and noncatalyzed reactions.

Authors:  Jarryl M D'Oyley; Abil E Aliev; Tom D Sheppard
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-21       Impact factor: 15.336

6.  Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols.

Authors:  Matthew N Pennell; Michael P Kyle; Samantha M Gibson; Louise Male; Peter G Turner; Richard S Grainger; Tom D Sheppard
Journal:  Adv Synth Catal       Date:  2016-04-27       Impact factor: 5.837

7.  Synthesis of "All-Cis" Trihydroxypiperidines from a Carbohydrate-Derived Ketone: Hints for the Design of New β-Gal and GCase Inhibitors.

Authors:  Maria Giulia Davighi; Francesca Clemente; Camilla Matassini; Amelia Morrone; Andrea Goti; Macarena Martínez-Bailén; Francesca Cardona
Journal:  Molecules       Date:  2020-10-02       Impact factor: 4.411

8.  Synthesis of tetrahydro-β-carbolines from 2-indolylmethyl azides and propargylic alcohols.

Authors:  Haiting Yin; Qin Ma; Yushan Wang; Xiaoxia Gu; Zhijun Feng; Yunjun Wu; Ming Wang; Shaoyin Wang
Journal:  RSC Adv       Date:  2021-06-01       Impact factor: 3.361

Review 9.  Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones.

Authors:  Pakorn Bovonsombat; Punyanuch Sophanpanichkul; Satreerat Losuwanakul
Journal:  RSC Adv       Date:  2022-08-12       Impact factor: 4.036

10.  Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols.

Authors:  Haiting Yin; Yunjun Wu; Xiaoxia Gu; Zhijun Feng; Meifang Wang; Dexiang Feng; Ming Wang; Ziyang Cheng; Shaoyin Wang
Journal:  RSC Adv       Date:  2022-07-21       Impact factor: 4.036
  10 in total

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