Literature DB >> 26028784

A Silver(I)-Catalyzed Intramolecular Ficini's [2 + 2] Cycloaddition Employing Ynamides.

Xiao-Na Wang1, Zhi-Xiong Ma2, Jun Deng3, Richard P Hsung2.   

Abstract

An intramolecular [2 + 2] cycloaddition using N-sulfonyl substituted ynamides tethered to an enone motif is described here. This thermally driven [2 + 2] cycloaddition manifold can be catalyzed effectively using AgNTf2, and represents the first examples of an intramolecular Ficini reaction.

Entities:  

Keywords:  AgNTf2; Intramolecular [2 + 2] cycloaddition; and electrocyclic ring-opening; the Ficini reaction; ynamides

Year:  2015        PMID： 26028784      PMCID： PMC4444066          DOI： 10.1016/j.tetlet.2015.01.017

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  29 in total

1.  Cu(I)- and Cu(II)-catalyzed cyclo- and Michael addition reactions of unsaturated β-ketoesters.

Authors:  Christoph Schotes; Antonio Mezzetti
Journal:  J Org Chem       Date:  2011-06-15       Impact factor: 4.354

Review 2.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

3.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

4.  Asymmetric Diels-Alder and Ficini reactions with alkylidene β-ketoesters catalyzed by chiral ruthenium PNNP complexes: mechanistic insight.

Authors:  Christoph Schotes; Martin Althaus; Raphael Aardoom; Antonio Mezzetti
Journal:  J Am Chem Soc       Date:  2012-01-06       Impact factor: 15.419

5.  Enantioselective Ficini reaction: ruthenium/PNNP-catalyzed [2+2] cycloaddition of ynamides with cyclic enones.

Authors:  Christoph Schotes; Antonio Mezzetti
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-25       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.  Trans-selective radical silylzincation of ynamides.

Authors:  Elise Romain; Carolin Fopp; Fabrice Chemla; Franck Ferreira; Olivier Jackowski; Martin Oestreich; Alejandro Perez-Luna
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-27       Impact factor: 15.336

8.  A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition.

Authors:  Miguel Garzón; Paul W Davies
Journal:  Org Lett       Date:  2014-09-09       Impact factor: 6.005

9.  Preparation of (Z)-α,β-disubstituted enamides via palladium-catalyzed addition of boronic acids to ynamides.

Authors:  Yuanfa Yang; Lina Wang; Fang Zhang; Gangguo Zhu
Journal:  J Org Chem       Date:  2014-09-24       Impact factor: 4.354

10.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005
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  1 in total

1.  Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.

Authors:  Max Moskowitz; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336
  1 in total

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