An efficient method for cyclopentene annulation onto alpha,beta-unsaturated ketones: W(CO)(5)(L)-catalyzed 5-endo-dig cyclization of 6-siloxy-5-en-1-ynes.
[reaction: see text] A highly efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto alpha,beta-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)(5)(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.
Iwasawa
Nobuharu
N
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Japan. niwasawa@chem.titech.ac.jp
Miura
Tomoya
T
Kiyota
Koichi
K
Kusama
Hiroyuki
H
Lee
Kooyeon
K
Lee
Phil Ho
PH