Literature DB >> 15151420

CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Xianhua Pan1, Qian Cai, Dawei Ma.   

Abstract

The CuI-catalyzed coupling reaction of vinyl halides with amides or carbamates proceeds well at room temperature to 80 degrees C in dioxane to give enamides using N,N-dimethylglycine as the promoter and Cs(2)CO(3) as the base. The geometry of the C-C double bond is retained during the reaction course. [reaction: see text]

Entities:  

Year:  2004        PMID： 15151420     DOI： 10.1021/ol049464i

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


  18 in total

1.  Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

Authors:  M Shahjahan Kabir; Ojas A Namjoshi; Ranjit Verma; Michael Lorenz; V V N Phani Babu Tiruveedhula; Aaron Monte; Steven H Bertz; Alan W Schwabacher; James M Cook
Journal:  J Org Chem       Date:  2011-11-28       Impact factor: 4.354

2.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

3.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Authors:  Rodolfo Tello-Aburto; Emily M Johnson; Cheyenne K Valdez; William A Maio
Journal:  Org Lett       Date:  2012-04-04       Impact factor: 6.005

5.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

6.  A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors:  Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal:  Org Lett       Date:  2015-01-12       Impact factor: 6.005

7.  Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

Authors:  Barry M Trost; James J Cregg; Nicolas Quach
Journal:  J Am Chem Soc       Date:  2017-04-04       Impact factor: 15.419

8.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

9.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

10.  Stereospecific total synthesis of somocystinamide A.

Authors:  Takashi L Suyama; William H Gerwick
Journal:  Org Lett       Date:  2008-09-13       Impact factor: 6.005
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