Literature DB >> 21344651

Oxazolones in organocatalysis, new tricks for an old reagent.

Andrea-Nekane R Alba1, Ramon Rios.   

Abstract

Oxazolones or azlactones are among the most-common starting materials for the synthesis of quaternary amino acids. Since the seminal works of Steglich and co-workers until the recent examples from Ooi and co-workers, azlactones have been the focus of intense research. Oxazolones are also widely used in organometallic chemistry; however, with the "renaissance" of organocatalysis, this reagent has emerged as an important starting material for a broad range of new organocatalytic asymmetric methodologies. In this Focus Review, we aim to cover all of these new organocatalytic methodologies. We begin by discussing the dynamic kinetic resolution reactions developed with azlactones. Then, we disclose the organocatalytic rearrangements. Finally, we focus on the use of oxazolones as nucleophiles in organocatalytic processes.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2011        PMID: 21344651     DOI: 10.1002/asia.201000636

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  12 in total

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3.  Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction.

Authors:  Marianne Steurer; Kim L Jensen; Dennis Worgull; Karl Anker Jørgensen
Journal:  Chemistry       Date:  2011-12-07       Impact factor: 5.236

4.  Enantioselective cycloaddition of münchnones onto [60]fullerene: organocatalysis versus metal catalysis.

Authors:  Juan Marco-Martínez; Silvia Reboredo; Marta Izquierdo; Vanesa Marcos; Juan Luis López; Salvatore Filippone; Nazario Martín
Journal:  J Am Chem Soc       Date:  2014-02-10       Impact factor: 15.419

5.  Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach.

Authors:  Amin F M Fahmy; Amira A El-Sayed; Magdy M Hemdan
Journal:  Chem Cent J       Date:  2016-10-06       Impact factor: 4.215

6.  A Brønsted base-promoted diastereoselective dimerization of azlactones.

Authors:  Danielle L J Pinheiro; Gabriel M F Batista; Pedro P de Castro; Leonã S Flores; Gustavo F S Andrade; Giovanni W Amarante
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7.  Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.

Authors:  Andreas Eitzinger; Katharina Zielke; Michael Widhalm; Raphaël Robiette; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-05-04       Impact factor: 3.319

8.  Cross-trienamines in asymmetric organocatalysis.

Authors:  Kim Søholm Halskov; Tore Kiilerich Johansen; Rebecca L Davis; Marianne Steurer; Frank Jensen; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2012-07-30       Impact factor: 15.419

9.  Synthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes.

Authors:  María Martín-Rodríguez; Luis M Castelló; Carmen Nájera; José M Sansano; Olatz Larrañaga; Abel de Cózar; Fernando P Cossío
Journal:  Beilstein J Org Chem       Date:  2013-11-11       Impact factor: 2.883

Review 10.  1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis.

Authors:  Antonia Mielgo; Claudio Palomo
Journal:  Beilstein J Org Chem       Date:  2016-05-09       Impact factor: 2.883

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