Literature DB >> 23670915

Construction of optically active indolines by formal [4+1] annulation of sulfur ylides and N-(ortho-chloromethyl)aryl amides.

Qing-Qing Yang1, Qiang Wang, Jing An, Jia-Rong Chen, Liang-Qiu Lu, Wen-Jing Xiao.   

Abstract

Get asymmetric! Asymmetric [4+1] annulation of sulfur ylides and N-(ortho-chloromethyl)aryl amides allowed the formation of the desired cycloadduct with moderate to high yields and enantioselectivities (see scheme). The described strategy, taking advantage of chiral sulfur ylides, represents a direct procedure to access chiral 2-substituted indolines.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID: 23670915     DOI: 10.1002/chem.201300988

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

Authors:  M Todd Hovey; Christopher T Check; Alexandra F Sipher; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

2.  Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides.

Authors:  Nicole Meisinger; Lukas Roiser; Uwe Monkowius; Markus Himmelsbach; Raphaël Robiette; Mario Waser
Journal:  Chemistry       Date:  2017-03-27       Impact factor: 5.236

3.  Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides.

Authors:  Ting-Bi Hua; Cheng-Xiong Liu; Wei-Min Hu; Long Wang; Qing-Qing Yang
Journal:  Sci Rep       Date:  2021-01-22       Impact factor: 4.379

4.  Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles.

Authors:  Jing-Wen Kang; Xiang Li; Fei-Yu Chen; Yuan Luo; Shu-Cang Zhang; Bin Kang; Cheng Peng; Xu Tian; Bo Han
Journal:  RSC Adv       Date:  2019-04-17       Impact factor: 4.036

5.  Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Authors:  Anna Lee; Ashkaan Younai; Christopher K Price; Javier Izquierdo; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2014-07-15       Impact factor: 15.419

  5 in total

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