Literature DB >> 12630869

(Z)-alpha-haloacrylates: an exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates.

D K Barma1, Abhijit Kundu, Hongming Zhang, Charles Mioskowski, J R Falck.   

Abstract

(Z)-alpha-Fluoro-, (Z)-alpha-chloro-, and (Z)-alpha-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 degrees C.

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Year:  2003        PMID: 12630869     DOI: 10.1021/ja029938d

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


  7 in total

1.  Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of β-Fluoro Michael Acceptors.

Authors:  Thomas J O'Connor; F Dean Toste
Journal:  ACS Catal       Date:  2018-06-04       Impact factor: 13.084

2.  Generation of Nucleophilic Chromium Acetylides from gem-Trichloroalkanes and Chromium Chloride: Synthesis of Propargyl Alcohols.

Authors:  Dhurke Kashinath; Steve Tisserand; Narender Puli; John R Falck; Rachid Baati
Journal:  European J Org Chem       Date:  2010-04-01

3.  Fe(0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls: an environmentally friendly alternative to Cr(II).

Authors:  J R Falck; Romain Bejot; Deb K Barma; Anish Bandyopadhyay; Suju Joseph; Charles Mioskowski
Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

4.  Cascade synthesis of (E)-2-alkylidenecyclobutanols.

Authors:  J R Falck; Anish Bandyopadhyay; Narender Puli; Abhijit Kundu; L Manmohan Reddy; Deb K Barma; Anyu He; Hongming Zhang; Dhurke Kashinath; Rachid Baati
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

5.  Synthesis of β-Fluoro-α,β-Unsaturated Amides from the Fragmentation of Morpholine 3,3,3-Trifluoropropanamide by Grignard Reagents.

Authors:  Amna T Adam; Frank R Fronczek; David A Colby
Journal:  Org Lett       Date:  2020-03-17       Impact factor: 6.005

Review 6.  Asymmetric synthesis of naturally occurring spiroketals.

Authors:  B Rama Raju; Anil K Saikia
Journal:  Molecules       Date:  2008-08-28       Impact factor: 4.411

Review 7.  Ethyl dibromofluoroacetate: a versatile reagent for the synthesis of fluorinated molecules.

Authors:  Emilie David; Samuel Couve-Bonnaire; Philippe Jubault; Xavier Pannecoucke
Journal:  Tetrahedron       Date:  2013-10-21       Impact factor: 2.457

  7 in total

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