Literature DB >> 25181754

Helicene-like chiral auxiliaries in asymmetric catalysis.

P Aillard1, A Voituriez, A Marinetti.   

Abstract

This literature overview demonstrates that helically chiral ligands and organocatalysts have been largely neglected so far. However, a few recent studies on helical pyridine, the corresponding ammonium salts and N-oxides have highlighted the significant potential of these compounds as organocatalysts for Michael type additions, aldehyde propargylations, epoxide openings, and others. In addition, helicenes displaying a fused phosphole ring at the end of their polyaromatic structures, have been used as ligands in enantioselective gold promoted cycloisomerization reactions, giving both excellent catalytic activity and high enantiomeric excesses. These recent results are expected to stimulate further research on the catalytic applications of helically chiral auxiliaries in the next few years.

Entities:  

Year:  2014        PMID: 25181754     DOI: 10.1039/c4dt01935k

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  10 in total

1.  Phosphahelicenes: From Chiroptical and Photophysical Properties to OLED Applications.

Authors:  Keihann Yavari; Wylliam Delaunay; Nicolas De Rycke; Thibault Reynaldo; Paul Aillard; Monika Srebro-Hooper; Victoria Y Chang; Gilles Muller; Denis Tondelier; Bernard Geffroy; Arnaud Voituriez; Angela Marinetti; Muriel Hissler; Jeanne Crassous
Journal:  Chemistry       Date:  2019-03-12       Impact factor: 5.236

2.  Enantiomerically Pure 5,13-Dicyano-9-oxa[7]helicene: Synthesis and Study.

Authors:  Riddhi Gupta; Trevor A Cabreros; Gilles Muller; Ashutosh V Bedekar
Journal:  European J Org Chem       Date:  2018-09-15

3.  Merging polyacenes and cationic helicenes: from weak to intense chiroptical properties in the far red region.

Authors:  Romain Duwald; Johann Bosson; Simon Pascal; Stéphane Grass; Francesco Zinna; Céline Besnard; Lorenzo Di Bari; Denis Jacquemin; Jérôme Lacour
Journal:  Chem Sci       Date:  2019-12-05       Impact factor: 9.825

4.  A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1'-binaphthalene-2,2'-diamines (BINAMs).

Authors:  Youhei Takeda; Masato Okazaki; Yoshiaki Maruoka; Satoshi Minakata
Journal:  Beilstein J Org Chem       Date:  2015-01-05       Impact factor: 2.883

5.  Rational Design and Synthesis of [5]Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions.

Authors:  Kosuke Yamamoto; Takashi Shimizu; Kazunobu Igawa; Katsuhiko Tomooka; Go Hirai; Hiroshi Suemune; Kazuteru Usui
Journal:  Sci Rep       Date:  2016-11-08       Impact factor: 4.379

6.  Dihydrogen contacts observed by through-space indirect NMR coupling.

Authors:  Martin Dračínský; Michal Buchta; Miloš Buděšínský; Jana Vacek-Chocholoušová; Irena G Stará; Ivo Starý; Olga L Malkina
Journal:  Chem Sci       Date:  2018-08-13       Impact factor: 9.825

7.  Gas phase synthesis of [4]-helicene.

Authors:  Long Zhao; Ralf I Kaiser; Bo Xu; Utuq Ablikim; Wenchao Lu; Musahid Ahmed; Mikhail M Evseev; Eugene K Bashkirov; Valeriy N Azyazov; Marsel V Zagidullin; Alexander N Morozov; A Hasan Howlader; Stanislaw F Wnuk; Alexander M Mebel; Dharati Joshi; Gregory Veber; Felix R Fischer
Journal:  Nat Commun       Date:  2019-04-03       Impact factor: 14.919

8.  Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring.

Authors:  Daria I Tonkoglazova; Anna V Gulevskaya; Konstantin A Chistyakov; Olga I Askalepova
Journal:  Beilstein J Org Chem       Date:  2021-01-04       Impact factor: 2.883

9.  Thiahelicene-based inherently chiral films for enantioselective electroanalysis.

Authors:  Serena Arnaboldi; Silvia Cauteruccio; Sara Grecchi; Tiziana Benincori; Massimo Marcaccio; Alessio Orbelli Biroli; Giovanna Longhi; Emanuela Licandro; Patrizia Romana Mussini
Journal:  Chem Sci       Date:  2018-11-29       Impact factor: 9.825

10.  Stereochemical significance of O to N atom interchanges within cationic helicenes: experimental and computational evidence of near racemization to remarkable enantiospecificity.

Authors:  Geraldine M Labrador; Céline Besnard; Thomas Bürgi; Amalia I Poblador-Bahamonde; Johann Bosson; Jérôme Lacour
Journal:  Chem Sci       Date:  2019-06-18       Impact factor: 9.825

  10 in total

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