Literature DB >> 20151710

Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: versatile synthons for isoxazoles, beta-lactams, and gamma-amino alcohols.

Shibing Tang1, Jinmei He, Yongquan Sun, Liuer He, Xuegong She.   

Abstract

An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy-2-isoxazolines, which have been proved to be versatile synthons for isoxazles, beta-hydroxy oximes, and gamma-amino alcohols. Beta-lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from beta-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.

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Year:  2010        PMID: 20151710     DOI: 10.1021/jo1000065

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

1.  Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction.

Authors:  John M Knapp; Jie S Zhu; Alex B Wood; Mark J Kurth
Journal:  ACS Comb Sci       Date:  2012-01-03       Impact factor: 3.784

2.  Development of methodologies for the regioselective synthesis of four series of regioisomer isoxazoles from β-enamino diketones.

Authors:  Raí G M Silva; Michael J V da Silva; Andrey P Jacomini; Sidnei Moura; Davi F Back; Ernani A Basso; Fernanda A Rosa
Journal:  RSC Adv       Date:  2018-01-25       Impact factor: 4.036

3.  Synthesis and Characterization of Novel Heterocyclic Chalcones from 1-Phenyl-1H-pyrazol-3-ol.

Authors:  Arminas Urbonavičius; Graziana Fortunato; Emilija Ambrazaitytė; Elena Plytninkienė; Aurimas Bieliauskas; Vaida Milišiūnaitė; Renzo Luisi; Eglė Arbačiauskienė; Sonata Krikštolaitytė; Algirdas Šačkus
Journal:  Molecules       Date:  2022-06-10       Impact factor: 4.927

4.  Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds.

Authors:  Gary A Molander; Steven R Wisniewski; Mona Hosseini-Sarvari
Journal:  Adv Synth Catal       Date:  2013-10-11       Impact factor: 5.837

5.  Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines.

Authors:  Melinda Nonn; Loránd Kiss; Reijo Sillanpää; Ferenc Fülöp
Journal:  Beilstein J Org Chem       Date:  2012-01-17       Impact factor: 2.883

6.  Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air.

Authors:  Min Li; Hong-Feng Xia; Li-Yao Yang; Tao Hong; Lin-Jie Xie; Shijun Li; Jing Wu
Journal:  RSC Adv       Date:  2019-03-20       Impact factor: 4.036

7.  Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones.

Authors:  Xue Cui; Jianting Ma; Tingting Zeng; Junyu Xu; Youbin Li; Xuesong Wang
Journal:  RSC Adv       Date:  2021-07-14       Impact factor: 4.036

8.  Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction.

Authors:  Wen Yang; Yongqi Yao; Xin Yang; Yingying Deng; Qifu Lin; Dingqiao Yang
Journal:  RSC Adv       Date:  2019-03-18       Impact factor: 4.036

9.  Electrochemical Synthesis of Isoxazolines: Method and Mechanism.

Authors:  Samuel D L Holman; Alfie G Wills; Neal J Fazakerley; Darren L Poole; Diane M Coe; Leonard A Berlouis; Marc Reid
Journal:  Chemistry       Date:  2022-02-10       Impact factor: 5.020

10.  A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime.

Authors:  Raoni S B Gonçalves; Michael Dos Santos; Guillaume Bernadat; Danièle Bonnet-Delpon; Benoit Crousse
Journal:  Beilstein J Org Chem       Date:  2013-11-07       Impact factor: 2.883

  10 in total

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