Efficient construction of the bicyclo[5.3.0]decenone skeleton based on the Rh(I)-catalyzed allenic Pauson-Khand reaction.
A reliable procedure for constructing a bicyclo[5.3.0]deca-1,7-dien-9-one ring system by rhodium-catalyzed Pauson-Khand reaction (PKR) of allenynes with a sulfonyl group has been developed. Investigation of the rhodium-catalyzed PKR on 19 examples of 1,2-nonadien-8-yne derivatives demonstrated that (i) acceptable yields could be consistently achieved through the proper choice of the rhodium catalyst ([RhCl(CO)(2)](2) or [RhCl(CO)dppp](2)) depending on the starting allenyne and that (ii) an ester functionality as well as hydroxy and siloxy groups could be tolerated in this rhodium-catalyzed PKR.
Mukai
Chisato
C
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi 13-1, Kanazawa 920-0934, Japan. cmukai@kenroku.kanazawa-u.ac.jp
Nomura
Izumi
I
Kitagaki
Shinji
S