Synlett 2007(19): 3055-3057  
DOI: 10.1055/s-2007-990964
LETTER
© Georg Thieme Verlag Stuttgart · New York

Tandem Conjugate Addition-Aldol Cyclization to give Optically Active 1-Aryl-1H-indenes via Asymmetric Pd2+-Catalyzed 1,4-Addition of Aryl-boronic Acids

Takashi Nishikataa, Yuri Kobayashib, Kenya Kobayshib, Yasunori Yamamotob, Norio Miyaura*b
a Innovation Plaza Hokkaido, Japan Science and Technology Agency, Sapporo 060-0819, Japan
b Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
Fax: +81(11)7066561; e-Mail: miyaura@eng.hokudai.ac.jp;
Further Information

Publication History

Received 19 September 2007
Publication Date:
08 November 2007 (online)

Abstract

An asymmetric 1,4-addition of arylboronic acids to β-(2-acylaryl)enones was carried out in aqueous isopropanol in the presence of a dicationic palladium(II) complex and HBF4. The palladium complexes of (S,S)-chiraphos gave optically active 1-aryl-1H-indenes of up to 97% ee via tandem 1,4-addition-aldol condensation.