Literature DB >> 15945110

Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds.

Jacob M Janey1.   

Abstract

The direct introduction of either a nitrogen or oxygen atom adjacent to a carbonyl group in a catalytic, enantioselective manner using both chiral Lewis acid and Lewis base catalysis has been described recently. The enantiomerically enriched products of these reactions, such as alpha-amino acids, represent fundamental building blocks for the construction of complex natural products and other important bioactive molecules. This Minireview provides a synopsis of this ever-growing field and highlights some of the challenges that still remain.

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Year:  2005        PMID: 15945110     DOI: 10.1002/anie.200462314

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


  21 in total

1.  A general approach to the enantioselective α-oxidation of aldehydes via synergistic catalysis.

Authors:  Scott P Simonovich; Jeffrey F Van Humbeck; David W C Macmillan
Journal:  Chem Sci       Date:  2012       Impact factor: 9.825

2.  Catalytic enantioselective O-H insertion reactions.

Authors:  Thomas C Maier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

3.  Organocatalysis in radical chemistry. Enantioselective alpha-oxyamination of aldehydes.

Authors:  Mukund P Sibi; Masayuki Hasegawa
Journal:  J Am Chem Soc       Date:  2007-03-16       Impact factor: 15.419

4.  Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors:  Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

5.  A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors:  Dillon H Miles; Joan Guasch; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

6.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

7.  Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis.

Authors:  Candice L Joe; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

8.  A sequential o-nitrosoaldol and Grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols.

Authors:  Peng Jiao; Masanori Kawasaki; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: a one-step synthesis of Plavix.

Authors:  Ryan W Evans; Jason R Zbieg; Shaolin Zhu; Wei Li; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-10-16       Impact factor: 15.419

10.  Regiochemical Reversals in Nitrosobenzene Reactions with Carbonyl Compounds: α-Aminooxyketone versus α-Hydroxyaminoketone Products.

Authors:  Donna J Nelson; Ravi Kumar
Journal:  European J Org Chem       Date:  2012-10
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