Literature DB >> 24186354

Enantioselective methodologies using N-carbamoyl-imines.

Jan Vesely1, Ramon Rios.   

Abstract

Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N-carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N-carbamoyl imines, focusing on synthetically useful protocols.

Entities:  

Year:  2014        PMID: 24186354     DOI: 10.1039/c3cs60321k

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  6 in total

1.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

2.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

3.  Enantioselective synthesis of α-tetrasubstituted (3-indolizinyl) (diaryl)methanamines via chiral phosphoric acid catalysis.

Authors:  Jialing Zhong; Rihuang Pan; Xufeng Lin
Journal:  RSC Adv       Date:  2022-07-15       Impact factor: 4.036

4.  Broad Spectrum Enolate Equivalent for Catalytic Chemo-, Diastereo-, and Enantioselective Addition to N-Boc Imines.

Authors:  Barry M Trost; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2015-12-14       Impact factor: 15.419

5.  Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles.

Authors:  Masahiro Torii; Kohsuke Kato; Daisuke Uraguchi; Takashi Ooi
Journal:  Beilstein J Org Chem       Date:  2016-09-28       Impact factor: 2.883

6.  Tyrosinase-mediated synthesis of larvicidal active 1,5-diphenyl pent-4-en-1-one derivatives against Culex quinquefasciatus and investigation of their ichthyotoxicity.

Authors:  SathishKumar Chidambaram; Daoud Ali; Saud Alarifi; Raman Gurusamy; SurendraKumar Radhakrishnan; Idhayadhulla Akbar
Journal:  Sci Rep       Date:  2021-10-20       Impact factor: 4.379

  6 in total

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