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Efficient Dibenzo[ c ]acridine Helicene-like Synthesis and Resolution: Scaleup, Structural Control, and High Chiroptical Properties

2011; American Chemical Society; Volume: 14; Issue: 1 Linguagem: Inglês

10.1021/ol202799j

1523-7060

Loı̈c Jierry, Steven Harthong, C. Aronica, Jean‐Christophe Mulatier, Laure Guy, Stéphan Guy,

Axial and Atropisomeric Chirality Synthesis

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–1cm2.