Literature DB >> 17288432

Highly enantioselective Michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides.

Kun Liu1, Han-Feng Cui, Jing Nie, Ke-Yan Dong, Xiao-Juan Li, Jun-An Ma.   

Abstract

[reaction: see text] A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).

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Year:  2007        PMID: 17288432     DOI: 10.1021/ol0701666

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


  7 in total

1.  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.

Authors:  Michael R Witten; Eric N Jacobsen
Journal:  Org Lett       Date:  2015-05-08       Impact factor: 6.005

Review 2.  Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Authors:  Elżbieta Wojaczyńska; Franz Steppeler; Dominika Iwan; Marie-Christine Scherrmann; Alberto Marra
Journal:  Molecules       Date:  2021-11-30       Impact factor: 4.411

3.  Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse Substituents: A Manifold of Hydrogen Bonding Networks.

Authors:  Joshua H Palmer; Gerard Parkin
Journal:  New J Chem       Date:  2014-09-01       Impact factor: 3.591

4.  Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity.

Authors:  Tatyana E Shubina; Matthias Freund; Sebastian Schenker; Timothy Clark; Svetlana B Tsogoeva
Journal:  Beilstein J Org Chem       Date:  2012-09-07       Impact factor: 2.883

5.  A New Class of Glucosyl Thioureas: Synthesis and Larvicidal Activities.

Authors:  Ping-An Wang; Jun-Tao Feng; Xing-Zi Wang; Mu-Qiong Li
Journal:  Molecules       Date:  2016-07-16       Impact factor: 4.411

Review 6.  Carbohydrates as enantioinduction components in stereoselective catalysis.

Authors:  Alexander S Henderson; John F Bower; M Carmen Galan
Journal:  Org Biomol Chem       Date:  2016-04-26       Impact factor: 3.876

Review 7.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411

  7 in total

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