Cyclization into hydrindanones using samarium diiodide
Samarium(II) iodide has been employed to promote vinylogous pinacol coupling reaction of aldehyde onto alpha,beta-unsaturated ketones. The diastereoselectivity of 6-endo products was changed by addition of a proton source and/or HMPA and by the reaction temperature. The cyclization reactions described herein provide a general approach to the syntheses of 3,3-dimethylhydrindanes with a cis-relationship between the OH at C-4 and the proton at C-3a with good diastereoselectivity and under mild reaction conditions.
Sono
M
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Nakashiba
Y
Nakashima
K
Tori
M