Literature DB >> 22176157

Efficient dibenzo[c]acridine helicene-like synthesis and resolution: scaleup, structural control, and high chiroptical properties.

Loïc Jierry1, Steven Harthong, Christophe Aronica, Jean-Christophe Mulatier, Laure Guy, Stéphan Guy.   

Abstract

Herein, we describe our recent expeditious synthesis of dibenzo[c]acridine helicene-like compounds on a large scale in pure enantiomeric form. This flexible synthesis allows for variation at several positions on the skeleton. Geometrical parameters related to these compounds have been obtained from monocrystal X-ray structure resolution. Additionally, chiroptical parameters have been recorded, highlighting the versatility of this family showing for example optical rotation at 589 nm varying between 135 and 150 deg g(-1)cm(2).
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID: 22176157     DOI: 10.1021/ol202799j

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


  3 in total

1.  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

2.  Synthesis of enantiomerically pure helicene like bis-oxazines from atropisomeric 7,7'-dihydroxy BINOL: Preliminary measurements of the circularly polarized luminescence.

Authors:  M Shyam Sundar; Harish R Talele; Hemant M Mande; Ashutosh V Bedekar; Roberto C Tovar; Gilles Muller
Journal:  Tetrahedron Lett       Date:  2014-03-01       Impact factor: 2.415

3.  Axial chiral bisbenzophenazines: solid-state self-assembly via halide hydrogen bonds triggered by linear alkanes.

Authors:  Alison E Metz; Erin E Podlesny; Patrick J Carroll; Ariel N Klinghoffer; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2014-07-18       Impact factor: 15.419

  3 in total

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