Literature DB >> 15151429

Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles.

Jodie L Brice1, James E Meerdink, Shannon S Stahl.   

Abstract

Palladium(II) complexes catalyze the formation of enamides via the formal cross-coupling reaction between nitrogen nucleophiles and vinyl ethers. These vinyl transfer reactions proceed in good yields with amide, carbamate, and sulfonamide nucleophiles, and the optimal catalyst is (DPP)Pd(OCOCF(3))(2) (DPP = 4,7-diphenyl-1,10-phenanthroline). [reaction: see text]

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Year:  2004        PMID： 15151429     DOI： 10.1021/ol0494360

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


  12 in total

1.  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

2.  Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

3.  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

4.  Decarbonylative approach to the synthesis of enamides from amino acids: stereoselective synthesis of the (Z)-aminovinyl-D-cysteine unit of mersacidin.

Authors:  Pablo García-Reynaga; Angela K Carrillo; Michael S VanNieuwenhze
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

5.  Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.

Authors:  Richard I McDonald; Gene W Wong; Ram P Neupane; Shannon S Stahl; Clark R Landis
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

6.  Synthesis and Characterization of Bimetallic Nanoclusters Stabilized by Chiral and Achiral Polyvinylpyrrolidinones. Catalytic C(sp3)-H Oxidation.

Authors:  Huafang Fan; Zongbo Tong; Zhaoyang Ren; Kanchan Mishra; Shunya Morita; Edruce Edouarzin; Lingaraju Gorla; Boris Averkiev; Victor W Day; Duy H Hua
Journal:  J Org Chem       Date:  2022-05-05       Impact factor: 4.198

7.  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

8.  A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Authors:  Pei-Yuan Yao; Yu Zhang; Richard P Hsung; Kang Zhao
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

9.  Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

10.  Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols.

Authors:  Stephanie G E Amos; Stefano Nicolai; Jerome Waser
Journal:  Chem Sci       Date:  2020-09-22       Impact factor: 9.825
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