Literature DB >> 15719090

Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions.

Juan R Dehli1, Julien Legros, Carsten Bolm.   

Abstract

For several decades, enamines and related compounds have been used as intermediates in organic synthesis and many methods are known for their preparation. Most of the synthetic protocols, however, require harsh reaction conditions. Recently, a new approach has emerged, inspired by the analogous arylation of amines catalysed by palladium or copper complexes (Buchwald-Hartwig reaction). Simultaneous and independent work from several research groups has led to the development of very powerful protocols for the preparation of enamines and their derivatives that require only readily available starting materials and proceed under very mild reaction conditions. Noteworthy is the fact that in less than five years an almost unknown reaction has reached such a high level of scope and generality that it is now very frequently applied in total syntheses of natural products.

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Year:  2005        PMID: 15719090     DOI: 10.1039/b415954c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  30 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.  General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors:  Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

3.  Diamine Ligands in Copper-Catalyzed Reactions.

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

4.  Activation of sp3 C-H bonds with cobalt(I): catalytic synthesis of enamines.

Authors:  Andrew D Bolig; Maurice Brookhart
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

Review 5.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Novel ynamide structural analogues and their synthetic transformations.

Authors:  Ting Lu; Richard P Hsung
Journal:  ARKIVOC       Date:  2014       Impact factor: 1.140

7.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

8.  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

9.  Stereospecific total synthesis of somocystinamide A.

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

10.  Parallel Synthesis of Structurally Diverse Aminobenzimidazole Tethered Sultams and Benzothiazepinones.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Tetrahedron Lett       Date:  2012-12-19       Impact factor: 2.415

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