Literature DB >> 21162555

Tandem cyclopropane ring-opening/Conia-ene reactions of 2-alkynyl indoles: a [3 + 3] annulative route to tetrahydrocarbazoles.

Huck K Grover1, Terry P Lebold, Michael A Kerr.   

Abstract

A Zn(NTf(2))(2) catalyzed tandem reaction consisting of a nucelophilic ring opening of 1,1-cyclopropanediesters by 2-alkynyl indoles followed by a Conia-ene ring closure results in the efficient one-step synthesis of tetrahydrocarbazoles. The adducts may be further elaborated to carbazoles.

Entities:  

Year:  2010        PMID： 21162555     DOI： 10.1021/ol102627e

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


  7 in total

1.  Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Authors:  Xiaochen Wang; Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

2.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

3.  A Ruthenium-Catalyzed Coupling of Alkynes with 1,3-Diketones.

Authors:  Megan K Pennington-Boggio; Brian L Conley; Travis J Williams
Journal:  J Organomet Chem       Date:  2012-05-25       Impact factor: 2.369

4.  Synthesis of tetrahydropyridazines by a metal-carbene-directed enantioselective vinylogous N-H insertion/Lewis acid-catalyzed diastereoselective Mannich addition.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-03       Impact factor: 15.336

5.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

6.  Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides.

Authors:  Rongli Zhang; Yanping Xia; Yuchen Yan; Lu Ouyang
Journal:  BMC Chem       Date:  2022-03-18

7.  An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.

Authors:  Makoto Shimizu; Takayoshi Morimoto; Yusuke Yanagi; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036
  7 in total

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