Literature DB >> 19739617

Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

Hongyan Li1, Richard P Hsung.   

Abstract

Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-furans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-furans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.

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Year:  2009        PMID： 19739617      PMCID： PMC2813717          DOI： 10.1021/ol901860b

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


  40 in total

1.  Thermally induced cyclopropene-carbene rearrangements: an overview.

Authors:  Mark S Baird
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

3.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

Authors:  Carole Alayrac; Dieter Schollmeyer; Bernhard Witulski
Journal:  Chem Commun (Camb)       Date:  2009-02-18       Impact factor: 6.222

5.  Rh-catalyzed intermolecular reactions of alkynes with alpha-diazoesters that possess beta-hydrogens: ligand-based control over divergent pathways.

Authors:  Patricia Panne; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

6.  Synthesis of tricyclic fused 3-aminopyridines through intramolecular Co(I)-catalyzed [2+2+2] cycloaddition between ynamides, nitriles, and alkynes.

Authors:  Pierre Garcia; Solenne Moulin; Yves Miclo; David Leboeuf; Vincent Gandon; Corinne Aubert; Max Malacria
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

7.  Dirhodium(II) tetra(N-(dodecylbenzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes.

Authors:  Huw M L Davies; Gene H Lee
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

8.  1,3-dialkyl-8-N-substituted benzyloxycarbonylamino-9-deazaxanthines as potent adenosine receptor ligands: Design, synthesis, structure-affinity and structure-selectivity relationships.

Authors:  Franco Fernández; Olga Caamaño; M Isabel Nieto; Carmen López; Xerardo García-Mera; Angela Stefanachi; Orazio Nicolotti; M Isabel Loza; Jose Brea; Cristina Esteve; Victor Segarra; Bernat Vidal; Angelo Carotti
Journal:  Bioorg Med Chem       Date:  2009-04-05       Impact factor: 3.641

9.  Application of ynamides in the synthesis of 2-amidoindoles.

Authors:  Karin Dooleweerdt; Thomas Ruhland; Troels Skrydstrup
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

10.  A general synthetic entry to the pentacyclic strychnos alkaloid family, using a [4 + 2]-cycloaddition/rearrangement cascade sequence.

Authors:  Jutatip Boonsombat; Hongjun Zhang; Majid J Chughtai; John Hartung; Albert Padwa
Journal:  J Org Chem       Date:  2008-04-01       Impact factor: 4.354
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  12 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

Review 3.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

4.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

5.  A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors:  Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

6.  Regioselective synthesis of multisubstituted furans via metalloradical cyclization of alkynes with α-diazocarbonyls: construction of functionalized α-oligofurans.

Authors:  Xin Cui; Xue Xu; Lukasz Wojtas; Martin M Kim; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

7.  Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2014-02-12       Impact factor: 6.222

8.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

9.  Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

Authors:  Xiaocong Xie; Yi Li; Joseph M Fox
Journal:  Org Lett       Date:  2013-03-20       Impact factor: 6.005

10.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
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