Literature DB >> 25710515

Gold(I)-catalyzed dearomative Rautenstrauch rearrangement: enantioselective access to cyclopenta[b]indoles.

Weiwei Zi1, Hongmiao Wu, F Dean Toste.   

Abstract

A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

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Year:  2015        PMID： 25710515      PMCID： PMC5087316          DOI： 10.1021/jacs.5b00613

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  43 in total

1.  Gold-catalyzed 1,3-addition of a sp3-hybridized C-H bond to alkenylcarbenoid intermediate.

Authors:  Sabyasachi Bhunia; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

2.  Recent advances in dearomatization of heteroaromatic compounds.

Authors:  Qiuping Ding; Xiaoli Zhou; Renhua Fan
Journal:  Org Biomol Chem       Date:  2014-07-21       Impact factor: 3.876

3.  Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors:  B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

4.  Interrupted imino-Nazarov cyclization of 1-aminopentadienyl cation and related cascade process.

Authors:  Ronny William; Siming Wang; Feiqing Ding; Elise Nerissa Arviana; Xue-Wei Liu
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-11       Impact factor: 15.336

5.  Rhodium-catalyzed [3 + 2] annulation of indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

6.  Regiodivergent synthesis of functionalized indene derivatives via Pt-catalyzed Rautenstrauch reaction of propargyl carbonates.

Authors:  Jinbo Zhao; Daniel A Clark
Journal:  Org Lett       Date:  2012-03-14       Impact factor: 6.005

7.  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

8.  Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Authors:  Gilles Lemière; Vincent Gandon; Kevin Cariou; Takahide Fukuyama; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Org Lett       Date:  2007-04-25       Impact factor: 6.005

9.  Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

10.  Nazarov reactions of vinyl cyclopropylamines: an approach to the imino-Nazarov problem.

Authors:  Sara A Bonderoff; Tina N Grant; F G West; Martin Tremblay
Journal:  Org Lett       Date:  2013-05-22       Impact factor: 6.005
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  14 in total

1.  Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors:  Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

2.  Diastereoselective synthesis and biological evaluation of enantiomerically pure tricyclic indolines.

Authors:  W He; B M Griffiths; W Wang; X Wang
Journal:  Org Biomol Chem       Date:  2017-05-16       Impact factor: 3.876

3.  Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates.

Authors:  Rebecca B Watson; Corinna S Schindler
Journal:  Org Lett       Date:  2017-12-20       Impact factor: 6.005

4.  Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

Authors:  Yugen Zhu; Wei He; Wei Wang; Chloe E Pitsch; Xiaotai Wang; Xiang Wang
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-23       Impact factor: 15.336

5.  Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.

Authors:  Zhiming Wang; Xingzhu Xu; Zhanshou Gu; Wei Feng; Houjun Qian; Zhengyi Li; Xiaoqiang Sun; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2016-02-14       Impact factor: 6.222

Review 6.  Recent metal-catalysed approaches for the synthesis of cyclopenta[b]indoles.

Authors:  Thavaraj Vivekanand; Bishnupada Satpathi; Siddheshwar K Bankar; S S V Ramasastry
Journal:  RSC Adv       Date:  2018-05-22       Impact factor: 4.036

7.  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

8.  Asymmetric construction of pyrido[1,2-a]-1H-indole derivatives via a gold-catalyzed cycloisomerization.

Authors:  Feng Jiang; Chunling Fu; Shengming Ma
Journal:  Chem Sci       Date:  2020-10-22       Impact factor: 9.825

9.  Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

Authors:  Chao Hu; Tao Wang; Matthias Rudolph; Thomas Oeser; Abdullah M Asiri; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

10.  Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

Authors:  Wen-Ting Wu; Ren-Qi Xu; Liming Zhang; Shu-Li You
Journal:  Chem Sci       Date:  2016-02-02       Impact factor: 9.825
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