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 Nishikata; Yuri Kobayashi; Kenya Kobayshi; Yasunori Yamamoto; Norio Miyaura

doi:10.1055/s-2007-990964

LETTER

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 Nishikata^a, Yuri Kobayashi^b, Kenya Kobayshi^b, Yasunori Yamamoto^b, 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;

Abstract

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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.

Key words

arylboronic acids - dicationic palladium catalyst - asymmetric conjugate addition - indene - tandem reactions

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