Literature DB >> 26508806

Rhodium-Catalyzed Intermolecular [5+1] and [5+2] Cycloadditions Using 1,4-Enynes with an Electron-Donating Ester on the 3-Position.

Casi M Schienebeck1, Wangze Song1, Angela M Smits1, Weiping Tang2.   

Abstract

Various 3-acyloxy-1,4-enynes could be employed in rhodium-catalyzed intermolecular [5+1] and [5+2] cycloadditions with CO or alkynes, respectively. The rate of these cycloadditions could be accelerated significantly by using 1,4-enynes with an electron-donating ester on the 3-position. The scope of rhodium-catalyzed [5+1] and [5+2] cycloadditions were examined by using 1,4-enynes bearing an electron-donating ester.

Entities:  

Keywords:  benzene; catalysis; cycloaddition; rhodium; rings

Year:  2015        PMID: 26508806      PMCID: PMC4617232          DOI: 10.1055/s-0034-1380160

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  20 in total

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Authors:  José Marco-Contelles; Elena Soriano
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

5.  Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.

Authors:  Casi M Schienebeck; Patrick J Robichaux; Xiaoxun Li; Lianqing Chen; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2013-04-04       Impact factor: 6.222

6.  Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors:  Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

7.  Rh-catalyzed [5+1] and [4+1] cycloaddition reactions of 1,4-enyne esters with CO: a shortcut to functionalized resorcinols and cyclopentenones.

Authors:  Takahide Fukuyama; Yuko Ohta; Célia Brancour; Kazusa Miyagawa; Ilhyong Ryu; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Chemistry       Date:  2012-04-13       Impact factor: 5.236

8.  Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Authors:  Xing-Zhong Shu; Casi M Schienebeck; Wangze Song; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-21       Impact factor: 15.336

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Authors:  Corinne Aubert; Louis Fensterbank; Pierre Garcia; Max Malacria; Antoine Simonneau
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

10.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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  5 in total

1.  Mechanism and Reactivity of Rh-Catalyzed Intermolecular [5+1] Cycloaddition of 3-Acyloxy-1,4-Enyne (ACE) and CO: A Computational Study.

Authors:  Xiao-Na Ke; Casi M Schienebeck; Chen-Chen Zhou; Xiufang Xu; Weiping Tang
Journal:  Chin Chem Lett       Date:  2015-03-27       Impact factor: 6.779

2.  Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Authors:  Xiaoxun Li; Haibo Xie; Xiaoning Fu; Ji-Tian Liu; Hao-Yuan Wang; Bao-Min Xi; Peng Liu; Xiufang Xu; Weiping Tang
Journal:  Chemistry       Date:  2016-06-20       Impact factor: 5.236

3.  Synthesis of Substituted Tropones by Sequential Rh-Catalyzed [5+2] Cycloaddition and Elimination.

Authors:  Wangze Song; Bao-Min Xi; Ka Yang; Weiping Tang
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

4.  Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Authors:  Xing-zhong Shu; Casi M Schienebeck; Xiaoxun Li; Xin Zhou; Wangze Song; Lianqing Chen; Ilia A Guzei; Weiping Tang
Journal:  Org Lett       Date:  2015-10-06       Impact factor: 6.005

Review 5.  Rhodium-Catalyzed (5 + 2) and (5 + 1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks.

Authors:  Stephanie A Blaszczyk; Daniel A Glazier; Weiping Tang
Journal:  Acc Chem Res       Date:  2019-12-10       Impact factor: 22.384

  5 in total

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