Synfacts 2006(3): 0230-0230  
DOI: 10.1055/s-2006-931939
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Helical Polyaryls

Contributor(s): Timothy M. Swager, Anne J. McNeil
T. Shibata*, K. Tsuchikama
Waseda University, Tokyo, Japan
Further Information

Publication History

Publication Date:
21 February 2006 (online)

Significance

A one-pot synthesis of axially chiral polyaryls through an Ir-catalyzed enantioselective [2+2+2] cycloaddition reaction is described. In this contribution, the authors extend the previously published Ir-catalyzed cycloaddition reaction to generate polyaryls with remarkable selectivity (T. Shibata, T. Fujimoto, K. Yokota, K. Takagi J. Am. Chem. Soc. 2004, 126, 8382-8383). Up to eight consecutive axial chiralities were controlled with >99% ee and 92% isolated yield. A polyaryl with the opposite helical sense could be obtained utilizing (R,R)-MeDUPHOS.