Literature DB >> 15200333

Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane.

Andrei V Malkov1, Andrea Mariani, Kenneth N MacDougall, Pavel Kocovský.   

Abstract

[reaction: see text] Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst and the incoming imine as the main factor determining the enantiofacial selectivity.

Entities:  

Year:  2004        PMID： 15200333     DOI： 10.1021/ol049213+

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


  4 in total

1.  Design and synthesis of 3,3'-triazolyl biisoquinoline N,N'-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles.

Authors:  Shiyu Sun; Carlyn Reep; Chenrui Zhang; Burjor Captain; Roberto Peverati; Norito Takenaka
Journal:  Tetrahedron Lett       Date:  2021-08-21       Impact factor: 2.032

2.  Disulfonimides versus Phosphoric Acids in Brønsted Acid Catalysis: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Reactivity.

Authors:  Kerstin Rothermel; Matej Žabka; Johnny Hioe; Ruth M Gschwind
Journal:  J Org Chem       Date:  2019-10-02       Impact factor: 4.354

3.  A one pot protocol to convert nitro-arenes into N-aryl amides.

Authors:  Elisabetta Massolo; Margherita Pirola; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  RSC Adv       Date:  2020-01-23       Impact factor: 4.036

4.  Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives.

Authors:  Martina Bonsignore; Maurizio Benaglia; Laura Raimondi; Manuel Orlandi; Giuseppe Celentano
Journal:  Beilstein J Org Chem       Date:  2013-04-02       Impact factor: 2.883
  4 in total

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