Literature DB >> 23784996

Remarkable configurational stability of magnesiated nitriles.

Graeme Barker1, Madeha R Alshawish, Melanie C Skilbeck, Iain Coldham.   

Abstract

Quaternary stereocenters: Chiral α-magnesiated nitriles can be formed by deprotonation and are configurationally stable at low temperature, even for acyclic examples. These can be trapped with electrophiles to give enantiomerically enriched quaternary substituted products (see scheme; TMP = 2,2,6,6-tetramethylpiperidine).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbanions; configurational stability; nitriles; organomagnesium compounds; stereoselectivity

Mesh：

Substances：

Year:  2013        PMID： 23784996     DOI： 10.1002/anie.201303442

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


  3 in total

1.  Highly enantioselective metallation-substitution alpha to a chiral nitrile.

Authors:  Arghya Sadhukhan; Melanie C Hobbs; Anthony J H M Meijer; Iain Coldham
Journal:  Chem Sci       Date:  2016-10-25       Impact factor: 9.825

Review 2.  Application of Biobased Solvents in Asymmetric Catalysis.

Authors:  Margherita Miele; Veronica Pillari; Vittorio Pace; Andrés R Alcántara; Gonzalo de Gonzalo
Journal:  Molecules       Date:  2022-10-08       Impact factor: 4.927

3.  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
  3 in total

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