Literature DB >> 23748437

Organocatalytic asymmetric remote aziridination of 2,4-dienals.

Kim Søholm Halskov1, Tricia Naicker, Magnus E Jensen, Karl Anker Jørgensen.   

Abstract

Highly regio- and stereoselective remote aziridination of 2,4-dienals has been developed, based on a vinylogous iminium-ion-dienamine catalytic cascade reaction. Transformations of the aziridine products into enantioenriched motifs are also demonstrated. Furthermore, the reaction concept is extended to include enantioselective 1,6-addition of thiols.

Entities:  

Year:  2013        PMID: 23748437     DOI: 10.1039/c3cc43506g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  5 in total

1.  Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

Authors:  Shea L Johnson; Michael K Hilinski
Journal:  J Org Chem       Date:  2019-06-19       Impact factor: 4.354

2.  Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

3.  Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones.

Authors:  Xiaodong Gu; Tingting Guo; Yuanyuan Dai; Allegra Franchino; Jie Fei; Chuncheng Zou; Darren J Dixon; Jinxing Ye
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-15       Impact factor: 15.336

4.  Old tricks, new dogs: organocatalytic dienamine activation of α,β-unsaturated aldehydes.

Authors:  Vanesa Marcos; José Alemán
Journal:  Chem Soc Rev       Date:  2016-11-02       Impact factor: 54.564

5.  Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry.

Authors:  Roelant Hilgers; Sin Yong Teng; Anamarija Briš; Aleksandr Y Pereverzev; Paul White; Jeroen J Jansen; Jana Roithová
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-03       Impact factor: 16.823

  5 in total

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