Literature DB >> 23407608

Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Fang-Le Hu1, Yin Wei, Min Shi, Suresh Pindi, Guigen Li.   

Abstract

The asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and with excellent enantioselectivity (90-99% ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems.

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Year:  2013        PMID: 23407608      PMCID: PMC3590110          DOI: 10.1039/c3ob27495k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  51 in total

1.  New Strategies for the Development of an Asymmetric Version of the Baylis-Hillman Reaction This work was supported by the Fonds der Chemischen Industrie (Liebig-scholarship and funds for P. L.). P. L. thanks Prof. Dr. A. de Meijere for his support.

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Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

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3.  Construction of chiral quaternary carbon through Morita-Baylis-Hillman reaction: an enantioselective approach to 3-substituted 3-hydroxyoxindole derivatives.

Authors:  Xiao-Yang Guan; Yin Wei; Min Shi
Journal:  Chemistry       Date:  2010-12-10       Impact factor: 5.236

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Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

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Journal:  J Org Chem       Date:  2012-03-22       Impact factor: 4.354

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Authors:  Katsuya Matsui; Shinobu Takizawa; Hiroaki Sasai
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

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Authors:  Wei Pei; Han-Xun Wei; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2002-10-21       Impact factor: 6.222

8.  N-phosphinyl imine chemistry (I): design and synthesis of novel N-phosphinyl imines and their application to asymmetric aza-Henry reaction.

Authors:  Suresh Pindi; Parminder Kaur; Gaurav Shakya; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2011-01       Impact factor: 2.817

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Review 10.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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  2 in total

1.  Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives.

Authors:  Radhey Mohan Singh; Kishor Chandra Bharadwaj; Dharmendra Kumar Tiwari
Journal:  Beilstein J Org Chem       Date:  2014-12-12       Impact factor: 2.883

Review 2.  Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts.

Authors:  Laura A Bryant; Rossana Fanelli; Alexander J A Cobb
Journal:  Beilstein J Org Chem       Date:  2016-03-07       Impact factor: 2.883

  2 in total

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