Literature DB >> 22733086

α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

Justin T Malinowski1, Ericka J Malow, Jeffrey S Johnson.   

Abstract

α-Aminations of ketone-derived nitrones have been developed via [3,3]-rearrangement of the intermediates generated upon condensation with imidoyl chlorides. Careful reagent selection provides synthetically attractive amino protecting groups. The enediamide or α'-carbamoyl enamide products can be hydrolyzed to the desired carbonyl, or exposed to electrophiles for further α-functionalization.

Entities:  

Year:  2012        PMID: 22733086      PMCID: PMC3545407          DOI: 10.1039/c2cc33401a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  17 in total

1.  Highly enantioselective organocatalytic α-amination reactions of aryl oxindoles: developing designer multifunctional alkaloid catalysts.

Authors:  Tommy Bui; Gloria Hernández-Torres; Ciro Milite; Carlos F Barbas
Journal:  Org Lett       Date:  2010-11-11       Impact factor: 6.005

2.  A general method for the alpha-acyloxylation of carbonyl compounds.

Authors:  Cory S Beshara; Adrian Hall; Robert L Jenkins; Kerri L Jones; Teyrnon C Jones; Niall M Killeen; Paul H Taylor; Stephen P Thomas; Nicholas C O Tomkinson
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

3.  Direct catalytic asymmetric alpha-amination of aldehydes.

Authors:  Benjamin List
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

4.  Rearrangement strategy for the synthesis of 2-aminoanilines.

Authors:  Achim Porzelle; Michael D Woodrow; Nicholas C O Tomkinson
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  Catalytic asymmetric direct alpha-amination reactions of 2-keto esters: a simple synthetic approach to optically active syn-beta-amino-alpha-hydroxy esters.

Authors:  Karsten Juhl; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

6.  A novel one-pot procedure for the stereoselective synthesis of alpha-hydroxy esters from ortho esters.

Authors:  Matthias Breuning; Tobias Häuser; Eva-Maria Tanzer
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

7.  Highly enantioselective and organocatalytic alpha-amination of 2-oxindoles.

Authors:  Liang Cheng; Li Liu; Dong Wang; Yong-Jun Chen
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

Review 8.  [3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products.

Authors:  Elizabeth A Ilardi; Craig E Stivala; Armen Zakarian
Journal:  Chem Soc Rev       Date:  2009-09-02       Impact factor: 54.564

9.  Copper-catalyzed electrophilic amination of diorganozinc reagents.

Authors:  Ashley M Berman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2004-05-12       Impact factor: 15.419

10.  Simple reaction conditions for the formation of ketonitrones from ketones and hydroxylamines.

Authors:  Jennifer Y Pfeiffer; André M Beauchemin
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

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