Literature DB >> 23435501

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

Casi M Schienebeck1, Patrick J Robichaux, Xiaoxun Li, Lianqing Chen, Weiping Tang.   

Abstract

We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most terminal alkynes.

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Year:  2013        PMID： 23435501      PMCID： PMC3610414          DOI： 10.1039/c3cc40634b

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


  28 in total

1.  The first intermolecular transition metal-catalyzed [5+2] cycloadditions with simple, unactivated, vinylcyclopropanes.

Authors:  P A Wender; C M Barzilay; A J Dyckman
Journal:  J Am Chem Soc       Date:  2001-01-10       Impact factor: 15.419

2.  The (4+3)-cycloaddition reaction: simple allylic cations as dienophiles.

Authors:  Michael Harmata
Journal:  Chem Commun (Camb)       Date:  2010-11-08       Impact factor: 6.222

Review 3.  Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters.

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

4.  Selectivity in nickel-catalyzed rearrangements of cyclopropylen-ynes.

Authors:  Gang Zuo; Janis Louie
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

5.  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

6.  Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes.

Authors:  Hermann A Wegner; Armin de Meijere; Paul A Wender
Journal:  J Am Chem Soc       Date:  2005-05-11       Impact factor: 15.419

7.  Mechanism and origins of ligand-controlled selectivities in [Ni(NHC)]-catalyzed intramolecular (5 + 2) cycloadditions and homo-ene reactions: a theoretical study.

Authors:  Xin Hong; Peng Liu; K N Houk
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

8.  Syntheses of seven-membered rings: ruthenium-catalyzed intramolecular [5+2] cycloadditions.

Authors:  Barry M Trost; Hong C Shen; Daniel B Horne; F Dean Toste; Bernhard G Steinmetz; Christopher Koradin
Journal:  Chemistry       Date:  2005-04-08       Impact factor: 5.236

9.  An atom-economic synthesis of bicyclo[3.1.0]hexanes by rhodium N-heterocyclic carbene-catalyzed diastereoselective tandem hetero-[5+2] cycloaddition/Claisen rearrangement reaction of vinylic oxiranes with alkynes.

Authors:  Jian-Jun Feng; Junliang Zhang
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

10.  A cheap metal for a "noble" task: preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes.

Authors:  Alois Fürstner; Keisuke Majima; Rubén Martín; Helga Krause; Egmont Kattnig; Richard Goddard; Christian W Lehmann
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419
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  10 in total

1.  Catalytic Efficiency Is a Function of How Rhodium(I) (5 + 2) Catalysts Accommodate a Conserved Substrate Transition State Geometry: Induced Fit Model for Explaining Transition Metal Catalysis.

Authors:  Thomas J L Mustard; Paul A Wender; Paul Ha-Yeon Cheong
Journal:  ACS Catal       Date:  2015-03-06       Impact factor: 13.084

2.  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

3.  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

4.  Rh-catalyzed (5+2) cycloadditions of 3-acyloxy-1,4-enynes and alkynes: computational study of mechanism, reactivity, and regioselectivity.

Authors:  Xiufang Xu; Peng Liu; Xing-zhong Shu; Weiping Tang; K N Houk
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419

5.  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

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

Authors:  Casi M Schienebeck; Wangze Song; Angela M Smits; Weiping Tang
Journal:  Synthesis (Stuttg)       Date:  2015-02-03       Impact factor: 3.157

Review 7.  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

8.  3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.

Authors:  Casi M Schienebeck; Xiaoxun Li; Xing-Zhong Shu; Weiping Tang
Journal:  Pure Appl Chem       Date:  2014-03-01       Impact factor: 2.453

9.  Computational Prediction of One-Step Synthesis of Seven-membered Fused Rings by (5+2) Cycloaddition Utilising Cycloalkenes.

Authors:  Chen-Chen Zhou; Xiao-Na Ke; Xiu-Fang Xu
Journal:  Sci Rep       Date:  2015-07-22       Impact factor: 4.379

10.  Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects.

Authors:  Gen-Qiang Chen; Wei Fang; Yin Wei; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825
  10 in total

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