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

Org Lett. 2012 Jan 6;14(1):288-91. doi: 10.1021/ol202799j. Epub 2011 Dec 16.

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).