Literature DB >> 25284248

β-Functionalization of carboxylic anhydrides with β-alkyl substituents through carbene organocatalysis.

Zhichao Jin1, Shaojin Chen, Yuhuang Wang, Pengcheng Zheng, Song Yang, Yonggui Robin Chi.   

Abstract

The first NHC-catalyzed functionalization of carboxylic anhydrides is described. In this reaction, the β carbon behaves as a nucleophilic carbon and undergoes asymmetric reactions with electrophiles. Anhydrides with challenging β-alkyl substituents work effectively.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbenes; anhydrides; asymmetric synthesis; organocatalysis; β-functionalization

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Year:  2014        PMID: 25284248     DOI: 10.1002/anie.201408604

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


  3 in total

1.  N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes.

Authors:  Lisa Candish; Alison Levens; David W Lupton
Journal:  Chem Sci       Date:  2015-01-26       Impact factor: 9.825

2.  A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.

Authors:  Zijun Wu; Jian Wang
Journal:  Chem Sci       Date:  2018-12-27       Impact factor: 9.825

3.  Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.

Authors:  Yan Li; Zhiqiang Zhang
Journal:  RSC Adv       Date:  2019-03-06       Impact factor: 4.036

  3 in total

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