Literature DB >> 21748834

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.

Xing-zhong Shu1, Suyu Huang, Dongxu Shu, Ilia A Guzei, Weiping Tang.   

Abstract

Rholling in the bicycles: a rhodium(I)-catalyzed cycloisomerization for the synthesis of bicyclic compounds containing a cycloheptatriene ring from linear alkenynes (see scheme; cod=1,5-cyclooctadiene) is proposed to proceed through 1,2-acyloxy migration, 6 π electrocyclization, migratory insertion, and reductive elimination. The overall process can be viewed as a novel intramolecular [5+2] cycloaddition with concomitant 1,2-acyloxy migration.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21748834      PMCID： PMC3399041          DOI： 10.1002/anie.201103136

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  63 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Asymmetric total synthesis of (+)-aphanamol I based on the transition metal catalyzed [5 + 2] cycloaddition of allenes and vinylcyclopropanes.

Authors:  P A Wender; L Zhang
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

3.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

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.  Palladium-catalyzed [3C + 2C + 2C] cycloaddition of enynylidenecyclopropanes: efficient construction of fused 5-7-5 tricyclic systems.

Authors:  Gaurav Bhargava; Beatriz Trillo; Marisel Araya; Fernando López; Luis Castedo; José L Mascareñas
Journal:  Chem Commun (Camb)       Date:  2009-11-27       Impact factor: 6.222

6.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

7.  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

8.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

9.  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

10.  A computationally designed Rh(I)-catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones.

Authors:  Yuanyuan Wang; Jingxin Wang; Jiachun Su; Feng Huang; Lei Jiao; Yong Liang; Dazhi Yang; Shiwei Zhang; Paul A Wender; Zhi-Xiang Yu
Journal:  J Am Chem Soc       Date:  2007-07-27       Impact factor: 15.419
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  23 in total

1.  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

2.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

3.  Rhodium-catalyzed carbonylation of 3-acyloxy-1,4-enynes for the synthesis of cyclopentenones.

Authors:  Xiaoxun Li; Suyu Huang; Casi M Schienebeck; Dongxu Shu; Weiping Tang
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

4.  Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Authors:  Xiaoxun Li; Hui Li; Wangze Song; Po-Sen Tseng; Lingyan Liu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-07       Impact factor: 15.336

5.  Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

Authors:  Tao Xu; Nikolas A Savage; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-20       Impact factor: 15.336

6.  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

7.  Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors:  Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

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

9.  Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

10.  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
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