Literature DB >> 24341407

C═N-containing azaarenes as activating groups in enantioselective catalysis.

Daniel Best, Hon Wai Lam.   

Abstract

Nitrogen-containing aromatic heterocycles (azaarenes) are of widespread chemical significance, and chiral compounds containing azaarenes feature prominently in pharmaceuticals, agrochemicals, and natural products. This Perspective highlights the use of a relatively underdeveloped strategy to prepare chiral azaarene-containing compounds: exploitation of the C═N bond embedded within certain azaarenes to activate adjacent functionality in catalytic asymmetric reactions. Work in this area has resulted in the development of several different types of catalytic enantioselective processes, including reductions, nucleophilic additions, and reductive couplings. It is hoped that this Perspective will encourage more researchers to work in this promising area.

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Year:  2014        PMID: 24341407     DOI: 10.1021/jo402414k

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  16 in total

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Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

3.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

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Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

4.  β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis.

Authors:  Katarzyna N Lee; Zhen Lei; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2017-03-30       Impact factor: 15.419

5.  Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.

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6.  Carbonylative N-Heterocyclization via Nitrogen-Directed C-C Bond Activation of Nonactivated Cyclopropanes.

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7.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

8.  Highly enantioselective catalytic synthesis of chiral pyridines.

Authors:  Ravindra P Jumde; Francesco Lanza; Tilde Pellegrini; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2017-12-12       Impact factor: 14.919

9.  Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations.

Authors:  Alan R Burns; Amaël G E Madec; Darryl W Low; Iain D Roy; Hon Wai Lam
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825

10.  Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.

Authors:  Jeffrey S Bandar; Erhad Ascic; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419

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