Literature DB >> 24245558

Regioselective functionalization of the oxazole scaffold using TMP-bases of Mg and Zn.

Diana Haas1, Marc Mosrin, Paul Knochel.   

Abstract

A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl·LiCl or TMPZnCl·LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.

Entities:  

Mesh:

Substances:

Year:  2013        PMID: 24245558     DOI: 10.1021/ol403019c

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  11-Step and Scalable Total Synthesis of Hamigeran M Enabled by Five C-H Functionalizations.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 16.383

2.  Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Authors:  Stacey L McDonald; Charles E Hendrick; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-25       Impact factor: 15.336

3.  Selective Functionalization of Tetrathiafulvalene Using Mg- and Zn-TMP-Bases: Preparation of Mono-, Di-, Tri-, and Tetrasubstituted Derivatives.

Authors:  Julia Nafe; Florian Auras; Konstantin Karaghiosoff; Thomas Bein; Paul Knochel
Journal:  Org Lett       Date:  2015-10-15       Impact factor: 6.005

4.  Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid.

Authors:  Kohei Yamada; Naoto Kamimura; Munetaka Kunishima
Journal:  Beilstein J Org Chem       Date:  2017-07-27       Impact factor: 2.883

5.  Silver Benzoate Facilitates the Copper-Catalyzed C-N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles.

Authors:  Cedric Lozano; Cristian Ramirez; Ny Sin; Hélène M-F Viart; Stanley B Prusiner; Nick A Paras; Jay Conrad
Journal:  ACS Omega       Date:  2021-03-31

6.  A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl.

Authors:  Moritz Balkenhohl; Harish Jangra; Ilya S Makarov; Shu-Mei Yang; Hendrik Zipse; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 16.823

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.