Literature DB >> 21390382

Mannich-Michael versus formal aza-Diels-Alder approaches to piperidine derivatives.

P Ricardo Girling1, Takao Kiyoi, Andrew Whiting.   

Abstract

A review into the aza-Diels-Alder reaction, mainly concentrating on literature examples that form piperidin-4-ones from the reaction of imines and electron rich dienes or enones, either through a Lewis acidic/Brønsted acid approach or through the use of an organocatalyst. This review questions whether the mechanism of the aza-Diels-Alder reaction is step wise as opposed to concerted when using oxygenated dienes.

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Year:  2011        PMID: 21390382     DOI: 10.1039/c0ob00996b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Authors:  Mathieu P Lalonde; Meredeth A McGowan; Naomi S Rajapaksa; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-01-28       Impact factor: 15.419

2.  The redox-Mannich reaction.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-23       Impact factor: 6.005

3.  Screening of metal ions and organocatalysts on solid support-coupled DNA oligonucleotides guides design of DNA-encoded reactions.

Authors:  Marco Potowski; Florian Losch; Elena Wünnemann; Janina K Dahmen; Silvia Chines; Andreas Brunschweiger
Journal:  Chem Sci       Date:  2019-11-01       Impact factor: 9.825

4.  Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor.

Authors:  Yuki Naito; Naoki Shida; Mahito Atobe
Journal:  Beilstein J Org Chem       Date:  2022-03-29       Impact factor: 2.883

5.  Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.

Authors:  Xiang Wu; Shi-Bao Zhao; Lang-Lang Zheng; You-Gui Li
Journal:  Molecules       Date:  2018-09-01       Impact factor: 4.411

6.  Concise Chemoenzymatic Three Step Total Synthesis of Isosolenopsin Through Medium Engineering.

Authors:  Robert C Simon; Christine S Fuchs; Horst Lechner; Ferdinand Zepeck; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2013-06-01
  6 in total

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