We thank the National Basic Research Program (2011CB932501), and the National Natural Science Foundation of China (21272264, 21332008) for financial support.
Dioxygen-Triggered Transannular Dearomatization of Benzohelicene Diols: Highly Efficient Synthesis of Chiral π-Extended Diones†
Article first published online: 1 APR 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 126, Issue 18, pages 4736–4739, April 25, 2014
How to Cite
Shen, Y., Lu, H.-Y. and Chen, C.-F. (2014), Dioxygen-Triggered Transannular Dearomatization of Benzohelicene Diols: Highly Efficient Synthesis of Chiral π-Extended Diones. Angew. Chem., 126: 4736–4739. doi: 10.1002/ange.201400486
- Issue published online: 25 APR 2014
- Article first published online: 1 APR 2014
- Manuscript Revised: 26 FEB 2014
- Manuscript Received: 16 JAN 2014
- National Basic Research Program. Grant Number: 2011CB932501
- National Natural Science Foundation of China. Grant Numbers: 21272264, 21332008
Oxidative dearomatization is a powerful strategy in organic synthesis. However, reports on using dioxygen as the oxidant, as it is environmentally friendly, readily available (air), and easy to handle, are rather limited. Helicene diols can undergo transannular dearomatization triggered by dioxygen to give diones in quantitative yields within several minutes. By virtue of this, the chirality is successfully transferred from helicity to central chirality to form distorted π-extended diones having two all-carbon quaternary stereocenters. The optical resolution was achieved by column chromatography, and the structures and the absolute configurations of the chiral diones were determined by X-ray analysis.