Literature DB >> 24802937

Catalytic asymmetric synthesis of 3,3'-diaryloxindoles as triarylmethanes with a chiral all-carbon quaternary center: phase-transfer-catalyzed S(N)Ar reaction.

Seiji Shirakawa1, Kenta Koga, Takashi Tokuda, Kenichiro Yamamoto, Keiji Maruoka.   

Abstract

Catalytic asymmetric synthesis of unsymmetrical triarylmethanes with a chiral all-carbon quaternary center was achieved by using a chiral bifunctional quaternary phosphonium bromide catalyst in the S(N)Ar reaction of 3-aryloxindoles under phase-transfer conditions. The presence of a urea moiety in the chiral phase-transfer catalyst was important for obtaining high enantioselectivity in this reaction.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arylation; asymmetric catalysis; organocatalysis; phase-transfer catalysis; synthetic methods

Mesh:

Substances:

Year:  2014        PMID: 24802937     DOI: 10.1002/anie.201403046

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


  3 in total

1.  C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr).

Authors:  Steven M Wales; Rakesh K Saunthwal; Jonathan Clayden
Journal:  Acc Chem Res       Date:  2022-05-27       Impact factor: 24.466

2.  Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates.

Authors:  Jinlong Qian; Jinlong Zhang; Huameng Yang; Lei Kang; Gaoxi Jiang
Journal:  Chem Sci       Date:  2019-08-07       Impact factor: 9.825

3.  Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes.

Authors:  Yuyu Cheng; Zhiqiang Fang; Yanwen Jia; Zhongyue Lu; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2019-08-05       Impact factor: 3.361

  3 in total

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