Volume 58, Issue 49 pp. 17625-17630
Communication

Atroposelective Arene Formation by Carbene-Catalyzed Formal [4+2] Cycloaddition

Ke Xu

Ke Xu

School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275 China

Search for more papers by this author
Wenchang Li

Wenchang Li

School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275 China

Search for more papers by this author
Shaoheng Zhu

Shaoheng Zhu

School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275 China

Search for more papers by this author
Prof. Dr. Tingshun Zhu

Corresponding Author

Prof. Dr. Tingshun Zhu

School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275 China

Search for more papers by this author
First published: 25 September 2019
Citations: 117

Graphical Abstract

Atroposelective [4+2]: A new organocatalyzed atroposelective arene formation reaction involves a carbene-catalyzed formal [4+2] cycloaddition of conjugated enals and α-aryl ketones. This study expands the synthetic potential of N-heterocyclic carbene (NHC) organocatalysis and provides a competitive pathway for the synthesis of axially chiral ligands, catalysts, and other functional molecules.

Abstract

Atroposelective arene formation is an efficient method to build axially chiral molecules with multi-substituted arenes. Reported here is an organocatalyzed atroposelective arene formation reaction by an N-heterocyclic carbene (NHC) catalyzed formal [4+2] cycloaddition of conjugated dienals and α-aryl ketones. This study expands the synthetic potential of NHC organocatalysis and provides a competitive pathway for the synthesis of axially chiral ligands, catalysts, and other functional molecules.

The full text of this article hosted at iucr.org is unavailable due to technical difficulties.