Literature DB >> 23150243

Dihydrooxazine oxides as key intermediates in organocatalytic Michael additions of aldehydes to nitroalkenes.

Gokarneswar Sahoo1, Hasibur Rahaman, Adám Madarász, Imre Pápai, Mikko Melarto, Arto Valkonen, Petri M Pihko.   

Abstract

Pause and play: dihydrooxazine oxides are stable intermediates that are protonated directly, without the intermediacy of the zwitterions, in organocatalytic Michael additions of aldehydes and nitroalkenes (see scheme, R=alkyl). Protonation of these species explains both the role of the acid co-catalyst in these reactions, and the observed stereochemistry when the reaction is conducted with α-alkylnitroalkenes.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID： 23150243     DOI： 10.1002/anie.201204833

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


  7 in total

1.  Additive and Emergent Catalytic Properties of Dimeric Unnatural Amino Acid Derivatives: Aldol and Conjugate Additions.

Authors:  María de Gracia Retamosa; Andrea Ruiz-Olalla; Maddalen Agirre; Abel de Cózar; Tamara Bello; Fernando P Cossío
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

2.  Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.

Authors:  Adam D Gammack Yamagata; Swarup Datta; Kelvin E Jackson; Linus Stegbauer; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

Review 3.  Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes.

Authors:  Diego A Alonso; Alejandro Baeza; Rafael Chinchilla; Cecilia Gómez; Gabriela Guillena; Isidro M Pastor; Diego J Ramón
Journal:  Molecules       Date:  2017-05-29       Impact factor: 4.411

4.  Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines.

Authors:  José R Martínez-Guillén; Jesús Flores-Ferrándiz; Cecilia Gómez; Enrique Gómez-Bengoa; Rafael Chinchilla
Journal:  Molecules       Date:  2018-01-11       Impact factor: 4.411

5.  NMR and Computational Studies on the Reactions of Enamines with Nitroalkenes That May Pass through Cyclobutanes.

Authors:  Alejandro Castro-Alvarez; Héctor Carneros; Jaume Calafat; Anna M Costa; Cristian Marco; Jaume Vilarrasa
Journal:  ACS Omega       Date:  2019-10-25

6.  A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E.

Authors:  Shinya Shiomi; Benjamin D A Shennan; Ken Yamazaki; Ángel L Fuentes de Arriba; Dhananjayan Vasu; Trevor A Hamlin; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2022-01-17       Impact factor: 15.419

7.  The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate.

Authors:  Weiqiang Chen; Huaquan Fang; Kaixue Xie; Martin Oestreich
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.236
  7 in total

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