Intermolecular Couplization and Cyclization of Chalcones Promoted by Samarium in DMF

Abstract

Under mild and neutral conditions, reductive coupling–cyclization of chalcones was promoted by samarium metal with an activator in DMF to afford products in good to excellent yields. The reaction is regioselective over the competitive carbon–carbon double-bond reduction and stereocontrolled.

Keywords:

• Chalcones
• cycntanols
• DMF
• samarium

ACKNOWLEDGMENT

This work was supported by the Foundation of the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (O4B0021400), the Natural Science Foundation of Shandong Province (No. Z2006B07), and the Project of Science and Technology of Shandong Province (No. 2006GG2203024).

Notes

^a Isolated yields, based on substrates.

^b A complicated mixture was afforded.

^c TMSCl was used instead of I₂.