Literature DB >> 12467411

Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.

Michele Badioli1, Roberto Ballini, Massimo Bartolacci, Giovanna Bosica, Elisabetta Torregiani, Enrico Marcantoni.   

Abstract

Readily preparable morpholine amides hitch in good yields with organocerium reagents to produce ketones. Even in the presence of substrates and reagents with high steric hindrance, the organometallic compounds prepared from dry cerium(III) chloride and organomagnesium or organolithium compounds at -78 degrees C add cleanly to morpholine amides. The low cost of starting materials makes this new scheme of synthesis very interesting for the preparation of biologically important pheromones.

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Year:  2002        PMID: 12467411     DOI: 10.1021/jo0263061

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

1.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors:  Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

2.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

3.  Nickel-Catalyzed Enantioselective Coupling of Aldehydes and Electron-Deficient 1,3-Dienes Following an Inverse Regiochemical Course.

Authors:  Thomas Q Davies; Jae Yeon Kim; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2022-10-04       Impact factor: 16.383

4.  The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-27       Impact factor: 15.336

5.  Generation and Trapping of Ketenes in Flow.

Authors:  Cyril Henry; David Bolien; Bogdan Ibanescu; Sally Bloodworth; David C Harrowven; Xunli Zhang; Andy Craven; Helen F Sneddon; Richard J Whitby
Journal:  European J Org Chem       Date:  2015-01-20

6.  Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.

Authors:  Shaozhong Ge; Sophie I Arlow; Michael G Mormino; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-10-03       Impact factor: 15.419

7.  Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.

Authors:  Kilian Colas; A Catarina V D Dos Santos; Stefanie V Kohlhepp; Abraham Mendoza
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

8.  Rh(I)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides.

Authors:  Kevin G M Kou; Diane N Le; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-06-17       Impact factor: 15.419

9.  Ca(OH)2-Catalyzed Condensation of Aldehydes with Methyl ketones in Dilute Aqueous Ethanol: A Comprehensive Access to α,β-Unsaturated Ketones.

Authors:  Lei Yu; Mengting Han; Jie Luan; Lin Xu; Yuanhua Ding; Qing Xu
Journal:  Sci Rep       Date:  2016-07-22       Impact factor: 4.379

10.  Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.

Authors:  Mario Leypold; Kyan A D'Angelo; Mohammad Movassaghi
Journal:  Org Lett       Date:  2020-10-13       Impact factor: 6.005

  10 in total

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